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.
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
2 Oct 2026
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.
18 Sept 2026
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
4 Sept 2026
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.
21 Aug 2026
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
7 Aug 2026
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
17 Jul 2026
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
3 Jul 2026
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
19 Jun 2026
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
5 Jun 2026
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
15 May 2026
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
1 May 2026
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
17 Apr 2026
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.
3 Apr 2026
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.
20 Mar 2026
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.
6 Mar 2026
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.
17 Feb 2026
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!
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Apple Podcasts (US)
5.0 / 5
3 ratings
Spotify
5.0 / 5
3 ratings
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