How I Started: Lessons from Entrepreneurs to the Next Generation

In this episode of Startup Standouts, host Samantha White interviews young entrepreneurs James and Landon, who run the Cauley Farm Shop.

They discuss their journey at Kids Markets, sharing insights on their product offerings, market experiences, and growth as business owners. The boys highlight their strategies for engaging customers, the importance of teamwork, and offer valuable advice for other kids interested in entrepreneurship.

Key topics:

• Testing products and adapting
• Increasing in confidence
• The importance of free samples and bringing people into the booth
• Persistence is key
• The soap making process and mentorship

#childrenentrepreneurship #marketexperience #youngbusinessowners #producttesting #salesstrategies #customerengagement #teamwork #adviceforkids #smallbusiness #youthentrepreneurship

Manny arrived in the United States at 13 years old with no money, no English, and no clear path.

What he did have was a willingness to work, pay attention, and take responsibility for his own progress. In this episode of How I Started, Manny Medina, Cuban American entrepreneur, investor, and founder of Medina Capital, shares how early lessons delivering newspapers at 4:30 a.m. shaped the mindset that later helped him build and scale major businesses, adapt across industries, and invest in the next generation of innovators.

This conversation is a reminder that progress often starts quietly, through consistent effort and personal responsibility, and that building something meaningful is possible even when you begin far behind.

Things You Will Learn

1. How early curiosity and persistence can turn small hustles into big business success.
2. Why adaptability and learning from mistakes is key to thriving in changing markets.
3. How embracing emerging technologies, like AI, opens new opportunities for young entrepreneurs.

Tools & Frameworks Covered

1. Curiosity-Driven Learning – Teaches how to leverage observation and questioning for opportunities.
2. Adaptability & Pivoting – Helps navigate changing industries and unexpected challenges.
3. Value Creation Mindset – Shows how to turn small efforts into meaningful results for others and yourself.

#Entrepreneurship #CuriositySuccess #Adaptability #MedinaLessons #HowIStartedPodcast

In this inspiring interview, 14-year-old entrepreneur Peter Lawton shares his journey from lawn mowing to running a successful 3D printing business called Panda Prints by Peter. Peter has been an entrepreneur since he was just nine years old. He’s tried different products, different marketing tactics, and manages everything himself. Discover how he navigates challenges, understands customer preferences, and leverages market insights to grow his business at kids markets.

Guest Links:

https://www.instagram.com/pandaprintsbypeter/

Key topics:

• Entrepreneurship at a young age
• Product testing and market adaptation
• Customer engagement strategies

#lawnmowing #smallbusiness #teenownedbusiness #youthentrepreneurship #3dprintingbusiness #kidsmarkets #businessgrowth #customerengagement #producttesting #entrepreneuriallessons

A small start can shape an entire founder journey, and this episode shows exactly how that happens. In this episode of How I Started, host Connor Boyack sits down with Chris Koerner to explore how entrepreneurship often begins with curiosity, quick action, and a willingness to test simple ideas before feeling fully ready.

Chris shares how he started a business as a kid, how that mindset stayed with him over time, and how he learned to grow a business by moving fast, noticing overlooked opportunities, and learning from mistakes. The conversation also explores startup pivots, practical takeaways, and why youth entrepreneurship matters in a world where adaptability, mentorship, and action can change a trajectory.

Things You Will Learn

1. How to start a business by acting on opportunities that others ignore
2. Why choosing the right type of business matters for long-term success
3. How testing ideas quickly can help founders learn and adapt faster
4. The mindset that helps founders act on opportunities early
5. How to recognize which business models fit your strengths and which do not

Tools & Frameworks Covered

1. Bias for action: helps you move from idea to execution without waiting too long
2. Surface area: helps you create more chances to learn by testing more ideas
3. Parkinson’s Law: helps you increase output by tightening the space available for tasks

#Entrepreneurship #FounderJourneys #YouthEntrepreneurship #StartABusiness #GrowABusiness

Kinsley has packed a lot of passion into her business. After realizing there was a need for heartfelt greeting cards, she built a business around the idea of connecting people through real moments, not just a text from your phone. Kinsley has built an incredible community at the Kids Markets, and has many lessons to share. In this episode, she shares her love for her business, advice she has received and given, and how to is expanding her business.

Guest Links:

https://kinsleyayn.com/

Key topics:

• Diversifying product offerings can attract a broader customer base.
• Enjoying your work is essential for long-term success and fulfillment.
• Building connections with others can enhance your business journey.

#GreetingCardBusiness #YouthEntrepreneur #HandmadeProducts #SmallBusiness #OrlandoSmallBusiness #HandmadeArt

Every entrepreneur has a starting point, and sometimes it begins with something as simple as a paper bag of potatoes.

In this episode of How I Started, host Connor Boyack sits down with Jeff Harmon, Co-founder of Harmon Brothers and Chief Content Officer at the Angel Studio, to explore how a small childhood business eventually led to the creation of Angel.

Jeff shares how he started selling potatoes at age eleven to pay for school tuition, what those early experiences taught him about solving problems, of mentorship, how founders learn through mistakes and pivots, and why noticing problems others ignore can open unexpected opportunities.

Things You Will Learn

1. How Jeff Harmon’s first small business became the beginning of a lifelong path in entrepreneurship
2. Why noticing everyday problems can help entrepreneurs find opportunities to start a business
3. How mentorship, persistence, and experimentation shape founder journeys

Tools & Frameworks Covered

1. Pain as a signal for opportunity: how problems often reveal the next business idea
2. Testing small ideas quickly: learning what works before scaling a business
3. Runway in entrepreneurship: balancing early work or side hustles while building something bigger

#Entrepreneurship #FounderJourneys #YouthEntrepreneurship #Mentorship #StartABusiness

Tyler Grant has always loved cool rocks, he’s been collecting them since he was just 5 years old. When he discovered Kids Markets, he realized his hobby could turn into a profitable business. But to make sales and make money, he needed to be able to grow his inventory at wholesale price. Tyler walks us through how he was able to build connections and offers advice to anyone looking to do the same.

Guest Links:

https://www.instagram.com/tylers_rocks_and_gems/

Key topics:

• Building a network
• Building connections
• Personal growth
• Starting a business at any age
• The importance of treating people with respect

#Kidownedbusiness #YoungEntrepreneur #RocksandGems

Some of the most valuable business lessons don’t come from success but from the companies that don’t survive.

In this episode of How I Started, Connor Boyack sits down with chef, entrepreneur, and business builder Robert Irvine, who shares how a love for home economics and understanding unit costs became the foundation for his first companies.

Robert walks through his early seasoning business, the lessons learned from failure, why knowing your numbers matters more than motivation, and how discipline, mentorship, and product differentiation shape long-term success.

Listeners will learn how entrepreneurial thinking applies far beyond startups, and why progress, not perfection, is what truly compounds over time.

Things You Will Learn

• How understanding costs early can prevent common founder mistakes
• Why product differentiation matters more than passion alone
• How entrepreneurial thinking applies beyond running your own business

Tools & Frameworks Covered

• Unit Cost Analysis – helps founders price products sustainably
• Market Differentiation Thinking – clarifies why your product exists
• Early Market Testing (Fairs & Pop-Ups) – validates demand before scaling

#Entrepreneurship #FounderJourney #BusinessLessons #StartupMindset #HowIStarted

However, it soon became apparent she needed to make a significant change in order to continue to grow her business.

Sawyer shares the stories of her very first sales and how she learned a whole new skill for the sake of her business, The Bead Borough.

Guest Links:

• https://www.facebook.com/profile.php?id=100091766717247
• https://www.instagram.com/p/DX4zQr_iefc/

Key topics:

1. Youth entrepreneurship
2. Crochet business
3. Learning new skills
4. Making the first sale

#BeadBorough #YouthEntrepreneur #CrochetBusiness #MarketVendor

Building something meaningful often begins with a small win, a lot of doubt, and the decision to keep going anyway. In this episode, Connor Boyack sits down with Christina Tosi, founder of Milk Bar and bestselling cookbook author, to talk honestly about how her love for baking slowly turned into a real business.

Christina shares the early moments that shaped her confidence, the lessons she learned working for others before betting on herself, and the hard decisions that helped Milk Bar stand out in an industry crowded with look-alikes. This conversation is a reminder that success isn’t about following a perfect path, it’s about paying attention, adjusting when things don’t work, and staying true to what makes your idea worth building.

Things You Will Learn

• How to differentiate in a crowded market without reinventing the category
• Why early validation and competition can shape long-term entrepreneurial thinking
• How goal setting creates clarity while still leaving room for flexibility

Tools & Frameworks Covered

• White Space Thinking – Helps founders adapt strategy without abandoning the vision
• Goal-Post Method – Turning long-term dreams into achievable short-term targets
• Differentiation Framework – Creating value in industries filled with similar products

#FounderJourney #EntrepreneurMindset #StartupStories #CreativeEntrepreneur #HowIStarted