<![CDATA[How to Make a Few Thousand Dollars]]>Frederick Ott and Sammy Mattingly host entrepreneurs, go-getters, goal setters, and risk takers in the new series "How to Make a Few Thousand Dollars." By touching on what these people are building, how they define success, and how they go about making a few thousand dollars, we hope to inspire listeners to chase their dreams and take action.

]]>https://www.mattinglyott.com/Riverside.fm (https://riverside.com)Mon, 02 Nov 2026 17:49:50 GMTTue, 17 Feb 2026 15:19:54 GMT60Frederick Ott<p>Frederick Ott and Sammy Mattingly host entrepreneurs, go-getters, goal setters, and risk takers in the new series "How to Make a Few Thousand Dollars." By touching on what these people are building, how they define success, and how they go about making a few thousand dollars, we hope to inspire listeners to chase their dreams and take action.</p>episodicFrederick Ottfred@mattinglyott.comno<![CDATA[Episode 17: Kahlil Garmon - Founder of MoneyBot]]>In this episode, Frederick Ott and Sammy Mattingley engage with Khalil, discussing the evolution of Moneybot, its unique approach to financial education, and the challenges of scaling the business. Khalil shares insights on clarity in business focus, the importance of understanding user needs, and strategies for growth.


Takeaways

  • Clarity drives business success
  • Engagement is key in education


Chapters

  • 00:00 Navigating the Madness of Entrepreneurship
  • 03:34 Defining Moneybot's Unique Value Proposition
  • 06:27 Engaging Schools and Educators
  • 09:52 Understanding the Business Model
  • 11:41 Evolving Marketing Strategies
  • 13:20 The Importance of Customer Discovery
  • 17:49 Strategizing for Growth and User Acquisition
]]>d1c03b9f-3973-4a39-b949-e0e4aa0f6817Fri, 16 Oct 2026 18:03:37 GMT<p>In this episode, Frederick Ott and Sammy Mattingley engage with Khalil, discussing the evolution of Moneybot, its unique approach to financial education, and the challenges of scaling the business. Khalil shares insights on clarity in business focus, the importance of understanding user needs, and strategies for growth.</p><p><br /></p><p>Takeaways</p><ul><li>Clarity drives business success</li><li>Engagement is key in education</li></ul><p><br /></p><p>Chapters</p><ul><li>00:00 Navigating the Madness of Entrepreneurship</li><li>03:34 Defining Moneybot's Unique Value Proposition</li><li>06:27 Engaging Schools and Educators</li><li>09:52 Understanding the Business Model</li><li>11:41 Evolving Marketing Strategies</li><li>13:20 The Importance of Customer Discovery</li><li>17:49 Strategizing for Growth and User Acquisition</li></ul>no00:21:56Episode 17: Kahlil Garmon - Founder of MoneyBotfull<![CDATA[Episode 16: Izzy Sanchez - One Louisville]]>This week on How to Make a Few Thousand Dollars, we sit down with Isai "Izzy" Sanchez, Director of Innovation at One Louisville (onelouisville.org), the region's economic development organization and chamber of commerce. Izzy talks through his early career in commercial real estate and residential single-family homes, and how that path led him into the public-private world at One Louisville. He also shares his advice for young people who want to build something, including why you should chase your ideas even when they sound crazy.

]]>3ca888a9-6e97-4ca0-b410-e88a9b368431Fri, 02 Oct 2026 13:00:00 GMT<p>This week on <i><em>How to Make a Few Thousand Dollars</em></i>, we sit down with Isai "Izzy" Sanchez, Director of Innovation at One Louisville (onelouisville.org), the region's economic development organization and chamber of commerce. Izzy talks through his early career in commercial real estate and residential single-family homes, and how that path led him into the public-private world at One Louisville. He also shares his advice for young people who want to build something, including why you should chase your ideas even when they sound crazy.</p>no00:26:47116Episode 16: Izzy Sanchez - One Louisvillefull<![CDATA[Episode 15: Ben Engel - Founder of JBT Cleanout]]>The conversation covers the journey of JBT Clean Out and its growth over the past six months. It delves into the challenges, strategies, and key takeaways from the experience, emphasizing the importance of building relationships and maintaining consistency in business operations.

Takeaways

  • Building strong relationships
  • Consistency in business operations

Chapters

  • 00:00 Business Growth and Adaptation
  • 03:00 The Power of Social Media
  • 06:02 Scaling the Business with Additional Staff
  • 07:56 Role of the Business Owner
  • 09:04 Balancing Time and Delegating Tasks
  • 11:49 Learning and Growth in Business
  • 14:48 Key Takeaways and Advice
]]>8d870811-ac0a-4666-a307-87518df25718Fri, 18 Sep 2026 13:00:00 GMT<p>The conversation covers the journey of JBT Clean Out and its growth over the past six months. It delves into the challenges, strategies, and key takeaways from the experience, emphasizing the importance of building relationships and maintaining consistency in business operations.</p><p></p><p>Takeaways</p><ul><li>Building strong relationships</li><li>Consistency in business operations</li></ul><p></p><p>Chapters</p><ul><li>00:00 Business Growth and Adaptation</li><li>03:00 The Power of Social Media</li><li>06:02 Scaling the Business with Additional Staff</li><li>07:56 Role of the Business Owner</li><li>09:04 Balancing Time and Delegating Tasks</li><li>11:49 Learning and Growth in Business</li><li>14:48 Key Takeaways and Advice</li></ul>no00:17:57115Episode 15: Ben Engel - Founder of JBT Cleanoutfull<![CDATA[Episode 14: Arclite]]>The episode features a conversation with the founders of ArcLite, Christian Carr and Brad Couch, who discuss their journey from corporate finance to entrepreneurship, the challenges of starting a business, and the emotional and technical aspects of building a cash flow management platform for small businesses.

Takeaways

  • Cash flow is a crucial variable in business decisions.
  • The emotional and logistical challenges of starting a business are significant.
]]>f9ade3b4-87b9-4b18-8ac0-e9093f4d175aFri, 04 Sep 2026 14:00:00 GMT<p>The episode features a conversation with the founders of ArcLite, Christian Carr and Brad Couch, who discuss their journey from corporate finance to entrepreneurship, the challenges of starting a business, and the emotional and technical aspects of building a cash flow management platform for small businesses.</p><p></p><p>Takeaways</p><ul><li>Cash flow is a crucial variable in business decisions.</li><li>The emotional and logistical challenges of starting a business are significant.</li></ul>no00:17:05114Episode 14: Arclitefull<![CDATA[Episode 13: Colin O'Daniel - Founder of Silk & Iron Co.]]>Colin O'Daniel shares his journey from college to entrepreneurship, including his experience in marketing, experiential marketing, and the founding of his own marketing agency, Highball. He also discusses the origin story of his clothing brand, Silk and Iron Co., and the challenges and successes he faced in launching the brand.

Takeaways

  • Entrepreneurial Journey
  • Challenges of Starting a Brand

Chapters

  • 00:00 Action and Operational Start of Silk and Iron
]]>f0c8b1f8-2a08-4b85-8020-9f27d1f6d472Fri, 21 Aug 2026 13:00:00 GMT<p>Colin O'Daniel shares his journey from college to entrepreneurship, including his experience in marketing, experiential marketing, and the founding of his own marketing agency, Highball. He also discusses the origin story of his clothing brand, Silk and Iron Co., and the challenges and successes he faced in launching the brand.</p><p></p><p>Takeaways</p><ul><li>Entrepreneurial Journey</li><li>Challenges of Starting a Brand</li></ul><p></p><p>Chapters</p><ul><li>00:00 Action and Operational Start of Silk and Iron</li></ul>no00:23:07113Episode 13: Colin O'Daniel - Founder of Silk & Iron Co.full<![CDATA[Episode 12: Tyler Durbin]]>Our conversation with Tyler delves into the balance between work and personal life, the advantages of remote work, embracing spontaneity and adventure, taking initiative in career development, overcoming the fear of change, networking and job search strategies, and closing thoughts and future plans.

Takeaways

  • Remote work enables flexibility and the opportunity for adventure.
  • Initiative and action are key to career development and job search success.

Chapters

  • 00:00 Exploring Work-Life Balance
  • 03:02 The Benefits of Remote Work
  • 06:03 Embracing Spontaneity and Adventure
  • 09:02 Taking Initiative in Career Development
  • 11:48 Overcoming Fear of Change
  • 15:00 Networking and Job Search Strategies
  • 24:05 Closing Thoughts and Future Plans
]]>b307bef7-547e-4ddd-8a73-05102b1f6d18Fri, 07 Aug 2026 13:00:00 GMT<p>Our conversation with Tyler delves into the balance between work and personal life, the advantages of remote work, embracing spontaneity and adventure, taking initiative in career development, overcoming the fear of change, networking and job search strategies, and closing thoughts and future plans.</p><p></p><p>Takeaways</p><ul><li>Remote work enables flexibility and the opportunity for adventure.</li><li>Initiative and action are key to career development and job search success.</li></ul><p></p><p>Chapters</p><ul><li>00:00 Exploring Work-Life Balance</li><li>03:02 The Benefits of Remote Work</li><li>06:03 Embracing Spontaneity and Adventure</li><li>09:02 Taking Initiative in Career Development</li><li>11:48 Overcoming Fear of Change</li><li>15:00 Networking and Job Search Strategies</li><li>24:05 Closing Thoughts and Future Plans</li></ul>no00:28:25Episode 12: Tyler Durbinfull<![CDATA[Episode 11: Graham Molinari - University of Louisville School of Medicine]]>The conversation covers the guest's experience in medical school, the curriculum, career paths in medicine, and the importance of work-life balance. It provides insights into the challenges and opportunities in the medical field, offering valuable advice for aspiring medical professionals.

Takeaways

  • Medical School Experience
  • Career Paths in Medicine

Chapters

  • 00:00 Introduction and Background
  • 01:29 Choosing a Medical School
  • 02:57 Medical School Curriculum
  • 09:37 Post-Graduation Career Options
  • 23:46 Balancing Work and Personal Life
]]>85e798a6-2a61-4e66-bd6c-91ccf7004915Fri, 17 Jul 2026 13:00:00 GMT<p>The conversation covers the guest's experience in medical school, the curriculum, career paths in medicine, and the importance of work-life balance. It provides insights into the challenges and opportunities in the medical field, offering valuable advice for aspiring medical professionals.</p><p></p><p>Takeaways</p><ul><li>Medical School Experience</li><li>Career Paths in Medicine</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction and Background</li><li>01:29 Choosing a Medical School</li><li>02:57 Medical School Curriculum</li><li>09:37 Post-Graduation Career Options</li><li>23:46 Balancing Work and Personal Life</li></ul>no00:31:29111Episode 11: Graham Molinari - University of Louisville School of Medicinefull<![CDATA[Episode 10: Quentin Hout - Policy Advisor, Office of Majority Leader Steve Scalise]]>The conversation covers a range of topics, including reconnecting with old friends, exploring career paths, finding an internship in DC, the influence of college experience, critical thinking and decision making, defining success, and career aspirations and advice.

Takeaways

  • Reconnecting with old friends can lead to interesting conversations and insights.
  • Success is an ongoing journey, and it's important to stay true to oneself while pursuing goals.

Chapters

  • 00:00 Reconnecting with Old Friends
  • 05:34 Influence of College Experience
  • 11:20 Defining Success
]]>b766487d-9910-43e0-b2ef-71a0af546ae8Fri, 03 Jul 2026 13:00:00 GMT<p>The conversation covers a range of topics, including reconnecting with old friends, exploring career paths, finding an internship in DC, the influence of college experience, critical thinking and decision making, defining success, and career aspirations and advice.</p><p></p><p>Takeaways</p><ul><li>Reconnecting with old friends can lead to interesting conversations and insights.</li><li>Success is an ongoing journey, and it's important to stay true to oneself while pursuing goals.</li></ul><p></p><p>Chapters</p><ul><li>00:00 Reconnecting with Old Friends</li><li>05:34 Influence of College Experience</li><li>11:20 Defining Success</li></ul>no00:22:25110Episode 10: Quentin Hout - Policy Advisor, Office of Majority Leader Steve Scalisefull<![CDATA[Episode 9: Surya Suresh - Co-founder of Aqqrue]]>Surya, co-founder of Aqqrue, shares his journey from private equity to entrepreneurship, highlighting the challenges and opportunities he encountered along the way. He discusses the impetus for starting Aqqrue and the vision for its success, providing valuable insights for aspiring entrepreneurs.

Takeaways

  • Transitioning from private equity to entrepreneurship
  • Identifying business opportunities and challenges in starting a business

Chapters

  • 00:00 Introduction and Background
  • 07:40 Identifying a Business Opportunity
  • 14:42 Defining Success for Accru
]]>ec686231-f785-45aa-b3c9-21f665585bf7Fri, 19 Jun 2026 13:00:00 GMT<p>Surya, co-founder of Aqqrue, shares his journey from private equity to entrepreneurship, highlighting the challenges and opportunities he encountered along the way. He discusses the impetus for starting Aqqrue and the vision for its success, providing valuable insights for aspiring entrepreneurs.</p><p></p><p>Takeaways</p><ul><li>Transitioning from private equity to entrepreneurship</li><li>Identifying business opportunities and challenges in starting a business</li></ul><p></p><p>Chapters</p><ul><li>00:00 Introduction and Background</li><li>07:40 Identifying a Business Opportunity</li><li>14:42 Defining Success for Accru</li></ul>no00:20:0819Episode 9: Surya Suresh - Co-founder of Aqqruefull<![CDATA[Episode 8: Chris Elder - Operator of Elder Construction]]>The conversation covers a diverse career trajectory, from early real estate interests to transitioning into construction. It explores the challenges faced, the growth of confidence, and the definition of success for Elder Construction. The advice provided emphasizes the importance of understanding one's motivations and finding balance in pursuing financial success.

Takeaways

  • Diverse Career Trajectory
  • Learning Through Experience

Chapters

  • 00:00 Early Career and Construction
  • 07:39 Transition into Construction
  • 12:56 Growth and Confidence
  • 19:30 Advice for Making Money
]]>651ea609-5cf8-4a3c-90f0-a857473d810eFri, 05 Jun 2026 13:00:00 GMT<p>The conversation covers a diverse career trajectory, from early real estate interests to transitioning into construction. It explores the challenges faced, the growth of confidence, and the definition of success for Elder Construction. The advice provided emphasizes the importance of understanding one's motivations and finding balance in pursuing financial success.</p><p></p><p>Takeaways</p><ul><li>Diverse Career Trajectory</li><li>Learning Through Experience</li></ul><p></p><p>Chapters</p><ul><li>00:00 Early Career and Construction</li><li>07:39 Transition into Construction</li><li>12:56 Growth and Confidence</li><li>19:30 Advice for Making Money</li></ul>no00:25:3418Episode 8: Chris Elder - Operator of Elder Constructionfull<![CDATA[Episode 7: Dan Ross-Li - Founder of LouDega]]>Dan Ross-Li — LouDega & The Power of Taking Action

We've known Dan for about a year, and his early advice was a turning point for us. Without it, we likely wouldn't have pivoted away from an earlier startup and ended up where we are now. So we were excited to finally get him on the show.

Dan is the founder of LouDega, a Louisville-based vending machine company he's actively growing. In this episode, we dig into his background, the career transitions that led him to entrepreneurship, and how he thinks about building businesses from the ground up.

The conversation centers on something Dan embodies better than almost anyone we know: an action-oriented mindset. For anyone considering the entrepreneurial path — or stuck overthinking their next move — Dan makes a compelling case that taking action consistently beats waiting for the perfect plan. He shares how he approaches idea execution, why staying close to the customer matters more than most founders realize, and what's next for LouDega.

If you're exploring whether to start something of your own, this one's worth your time.

Takeaways

  • Action beats planning — momentum is the real moat
  • Stay obsessively close to your customer
  • Pursue what you're genuinely drawn to, then execute relentlessly

Chapters

  • 00:00 — Introduction and meeting Dan
  • 06:35 — Founding LouDega and the KYX story
  • 12:15 — Where LouDega is headed
  • 23:06 — Dan's advice for anyone trying to make a few thousand dollars
]]>259517c4-5917-4e65-9abe-8ccf18939048Fri, 15 May 2026 13:00:00 GMT<p><b>Dan Ross-Li — LouDega &amp; The Power of Taking Action</b></p><p></p><p>We've known Dan for about a year, and his early advice was a turning point for us. Without it, we likely wouldn't have pivoted away from an earlier startup and ended up where we are now. So we were excited to finally get him on the show.</p><p></p><p>Dan is the founder of LouDega, a Louisville-based vending machine company he's actively growing. In this episode, we dig into his background, the career transitions that led him to entrepreneurship, and how he thinks about building businesses from the ground up.</p><p></p><p>The conversation centers on something Dan embodies better than almost anyone we know: an action-oriented mindset. For anyone considering the entrepreneurial path — or stuck overthinking their next move — Dan makes a compelling case that taking action consistently beats waiting for the perfect plan. He shares how he approaches idea execution, why staying close to the customer matters more than most founders realize, and what's next for LouDega.</p><p></p><p>If you're exploring whether to start something of your own, this one's worth your time.</p><p></p><p><b>Takeaways</b></p><ul><li>Action beats planning — momentum is the real moat</li><li>Stay obsessively close to your customer</li><li>Pursue what you're genuinely drawn to, then execute relentlessly</li><li></li></ul><p><b>Chapters</b></p><ul><li>00:00 — Introduction and meeting Dan</li><li>06:35 — Founding LouDega and the KYX story</li><li>12:15 — Where LouDega is headed</li><li>23:06 — Dan's advice for anyone trying to make a few thousand dollars</li></ul>yes00:26:1917Episode 7: Dan Ross-Li - Founder of LouDegafull<![CDATA[Episode 6: Brycen Harkins - Founder of Social Medians]]>In this episode, we sit down with a friend of the pod who built his own social media ad agency from scratch. We get into how his first job shaped the way he thinks about business, why he made the leap from employee to founder, and what that brutal first month actually looked like. He breaks down how he landed early clients, the systems he uses to stay organized, and where he's taking the agency next.

Takeaways:

  • How your first job shapes your founder instincts
  • What the leap from W-2 to entrepreneur really feels like
  • Surviving (and learning from) the first month
  • Practical client acquisition for a new agency
  • Staying organized when you're the whole team
  • Why betting on yourself is the prerequisite

Chapters

  • 00:00 Starting a Business Journey
  • 07:20 Challenges of the First Month
  • 13:02 Organization and Time Management
]]>2c87f76a-ef25-4801-86ca-f0370653cb24Fri, 01 May 2026 13:00:00 GMT<p>In this episode, we sit down with a friend of the pod who built his own social media ad agency from scratch. We get into how his first job shaped the way he thinks about business, why he made the leap from employee to founder, and what that brutal first month actually looked like. He breaks down how he landed early clients, the systems he uses to stay organized, and where he's taking the agency next.</p><p></p><p>Takeaways:</p><ul><li>How your first job shapes your founder instincts</li><li>What the leap from W-2 to entrepreneur really feels like</li><li>Surviving (and learning from) the first month</li><li>Practical client acquisition for a new agency</li><li>Staying organized when you're the whole team</li><li>Why betting on yourself is the prerequisite</li></ul><p></p><p>Chapters</p><ul><li>00:00 Starting a Business Journey</li><li>07:20 Challenges of the First Month</li><li>13:02 Organization and Time Management</li></ul>no00:20:4816Episode 6: Brycen Harkins - Founder of Social Mediansfull<![CDATA[Episode 5: Parker Norman - Founder of Evergreen Lawncare and Landscapes]]>In our conversation with Parker Norman, we discuss his entrepreneurial journey, from starting Evergreen Lawn Care and Landscapes to expanding services and considering future ventures like building a hockey rink. We explore his passion for hockey and refereeing, the transition to full-fledged lawncare service, and the development of communication skills. Parker shares his perspective on defining success and goals, emphasizing the journey aspect and the importance of helping people.

]]>67e1d730-94e6-4960-b1ca-7b2bf69d564cFri, 17 Apr 2026 13:00:00 GMT<p>In our conversation with Parker Norman, we discuss his entrepreneurial journey, from starting Evergreen Lawn Care and Landscapes to expanding services and considering future ventures like building a hockey rink. We explore his passion for hockey and refereeing, the transition to full-fledged lawncare service, and the development of communication skills. Parker shares his perspective on defining success and goals, emphasizing the journey aspect and the importance of helping people.</p>no00:28:1715Episode 5: Parker Norman - Founder of Evergreen Lawncare and Landscapesfull<![CDATA[Episode 4: Ben Engel - Founder of JBT Cleanout]]>We had the pleasure of sitting down with Ben Engel, one of the founders of JBT Cleanout. JBT Cleanout is a local residential and commercial cleanout business. Our conversation with Ben covers the journey of starting a business at a young age, the challenges and successes of building a business, the importance of networking, defining success, and finding happiness.

]]>2a262ec9-7bed-4f84-9f11-1e91cf9d6f66Fri, 03 Apr 2026 13:00:00 GMT<p>We had the pleasure of sitting down with Ben Engel, one of the founders of JBT Cleanout. JBT Cleanout is a local residential and commercial cleanout business. Our conversation with Ben covers the journey of starting a business at a young age, the challenges and successes of building a business, the importance of networking, defining success, and finding happiness.</p>no00:27:00Episode 4: Ben Engel - Founder of JBT Cleanoutfull<![CDATA[Episode 3: Kahlil Garmon - Founder of MoneyBot]]>Join us as we sit down with Kahlil Garmon, founder of MoneyBot. Our conversation covers a range of topics including idea creation, the importance of action in entrepreneurship, the sales process, defining success, and what makes you happy. Kahlil emphasizes building trust and personal connections in the sales process, and describes action as the separator in entrepreneurship.

]]>a6c56898-9434-470f-8dac-dfc0ac841810Fri, 20 Mar 2026 13:00:00 GMT<p>Join us as we sit down with Kahlil Garmon, founder of MoneyBot. Our conversation covers a range of topics including idea creation, the importance of action in entrepreneurship, the sales process, defining success, and what makes you happy. Kahlil emphasizes building trust and personal connections in the sales process, and describes action as the separator in entrepreneurship.</p>no00:29:4413Episode 3: Kahlil Garmon - Founder of MoneyBotfull<![CDATA[Episode 2: John King Jr. - Director of Trinity High School Annual Fund]]>Our conversation with John covers his role as Annual Fund Director at Trinity High School, his efforts to engage alumni and build a connected network across the country, and how he measures success and thinks about goal setting. John shares a unique perspective having spent the first part of his career in the corporate banking world before transitioning to the education space.

]]>4e2e6dea-d1a1-4e0b-b3d7-cf4e5352069cFri, 06 Mar 2026 14:00:00 GMT<p>Our conversation with John covers his role as Annual Fund Director at Trinity High School, his efforts to engage alumni and build a connected network across the country, and how he measures success and thinks about goal setting. John shares a unique perspective having spent the first part of his career in the corporate banking world before transitioning to the education space.</p>no00:20:10Episode 2: John King Jr. - Director of Trinity High School Annual Fundfull<![CDATA[Episode 1 - Tyler Durbin]]>Tyler Durbin, owner of the @tdfitclub social media channels, joins us on our first episode of How to Make a Few Thousand Dollars. Tyler discusses the purpose of tdfitclub, how he defines success in the context of what he's building, and what makes him happy. Tune in for free today!

]]>f4964dbc-86ed-4053-b5da-b0b220db3e95Tue, 17 Feb 2026 15:24:14 GMT<p>Tyler Durbin, owner of the @tdfitclub social media channels, joins us on our first episode of How to Make a Few Thousand Dollars. Tyler discusses the purpose of tdfitclub, how he defines success in the context of what he's building, and what makes him happy. Tune in for free today!</p>no00:24:3211Episode 1 - Tyler Durbinfull