How I Started: Lessons from Entrepreneurs to the Next Generation

Samantha White talks with Noa Schlosschberg, a 14-year-old candle maker in the Atlanta area, about how a candle-making class turned into a real business. Noa shares her early trial-and-error process, how Kids Markets helped her go from testing ideas to selling consistently, and what she’s learned about confidence, pricing, and standing out as a small business.

Guest Links:

https://www.instagram.com/hilomcandles/

Key topics:

• Building and growing a candle business

• Building Inventory

• Investing in your business

• Advise for young entrepreneurs

• Creating a cozy brand

#YoungEntrepreneur #TeenBusinessOwner #CandleMaking #SmallBusiness #SoyCandles #KidsMarkets #AtlantaEntrepreneur

What happens when you walk away from a steady job with no income, no plan, and no safety net? Bill Reynolds did exactly that in his twenties and spent the next six decades building one of the most enduring commercial real estate portfolios along Colorado's Front Range.

In this episode of How I Started, Bill, a longtime real estate developer and philanthropist funding the next generation of entrepreneurs, shares the real founder journey behind millions of square feet of offices, shops, and warehouses.

From shoveling snow for a quarter to personally signing on every loan to build his first buildings, Bill walks through the mountains he had to climb, the partnerships that shaped his path, and the failure that knocked him off his “cocky perch” early on.

Things You Will Learn

1. Why taking calculated risk is essential to entrepreneurship, and how Bill's higher tolerance for risk shaped six decades of real estate success.
2. How to choose a business partner by looking at their values first, not just their resources or skills.
3. Why a single major failure can become the most valuable lesson of your entire career, and how to use it to grow stronger.

Tools & Frameworks Covered

1. The Contribution Mindset: reframing work and jobs as contributing to family, community, and country to build the foundation for future success.
2. Burn-the-Boats Decision Making: removing your safety net to force focus and urgency, used by Bill when he left his father's business to start his own.
3. Values-First Partnership Selection: evaluating partners on aligned values rather than liquidity, since shared values carry partnerships through the inevitable hard decisions.

#FounderJourney #Entrepreneurship #YouthEntrepreneurship #StartABusiness #MentoringTheNextGeneration

This week, Samantha gets to talk to Elisheba Sam, an incredibly talented crochet artist with a unique range of products and amazing storytelling skills. She shares how she got into crochet, her experiences selling her more unusual products, and how she overcame unexpected setbacks to have success. You won’t want to miss this enthralling episode!

Guest Links:

https://www.instagram.com/freedomfam.us?stkn=aGZrZGhwYjI4Yjht

Key Topics

1. Youth entrepreneurship
2. Starting a handmade business as a child
3. Crochet entrepreneurship
4. Selling at children’s entrepreneur markets
5. Creating unique products
6. Product experimentation and innovation
7. Building confidence through sales
8. Overcoming fear and self-doubt
9. Handling slow markets and bad weather
10. Learning from business setbacks
11. Product presentation and booth displays
12. Understanding customer behavior
13. Finding a target audience
14. Selling plushies and crocheted weapons
15. Custom orders and online selling
16. Persistence and not giving up
17. Turning a hobby into a business
18. Creative problem-solving
19. The importance of customer feedback

#KidEntrepreneur #YoungEntrepreneur #CrochetBusiness #HandmadeBusiness #SmallBusiness #YoungCreators #EntrepreneurialMindset #CrochetMarket #OrlandoMarkets

What does it take to go from door-to-door card sales at age eight to building a multimillion-dollar catering company?

Mary Crafts, Founder of Mary Crafts Inc. and one of Utah's most recognized culinary entrepreneurs, joins host Connor Boyack to share the real founder journey behind decades of growth.

In this episode of How I Started, Mary walks us through her earliest entrepreneurial experience in a small Iowa town of 250 people, how watching her father identify community needs sparked her own instinct to create value, and how she turned home cooking and a red wagon into a thriving catering empire.

Things You Will Learn

1. How to identify a real need in your community and turn it into a business idea the same way Mary did at age eight and again when she launched her catering company
2. Why rejection of your product is never a rejection of you and how understanding that difference unlocks the confidence to start selling
3. How to discover what you're truly passionate about by noticing what makes people stop and listen when you speak

Tools & Frameworks Covered

1. The Need-First Business Model: spotting what a community is missing before building the product, used by both Mary and her father to find their markets
2. The Passion Discovery Method: identifying your entrepreneurial niche by asking what topics make others lean in and keep listening
3. The Value-First Selling Approach: leading with service and customer experience over profit, which Mary credits as the foundation of long-term business growth

#YouthEntrepreneurship #FounderJourney #StartABusiness #Entrepreneurship #MentoringTheNextGeneration

This week we get to speak with Wilfred Bailey, a 13-year-old entrepreneur behind Happy Face Creations, about turning a love of reading into a business selling custom bookmarks and stickers. Wilfred shares how he improved product quality, organized inventory with a POS system, and kept growing through market feedback, weather challenges, and constant iteration.

Guest Links:

• www.happyfacecreations.com
• https://www.instagram.com/happyfacecreations24/
• https://www.etsy.com/shop/HappyFaceCreation

Key topics:

• Building a bookmark business

• Focusing on quality

• Overcoming operational challenges

#bookmarkbusiness #youngentrepreneur #kidsmarkets #orlandomarkets #smallbusiness #operationaladvice #customorders #inventorytracking #POS #overcomingweatherchallenges #familysupport

What does it actually look like to grow a student side hustle into a company worth nearly $2 billion?

John Pestana did exactly that, starting by building websites for $20 an hour out of a college computer lab, and eventually selling Omniture to Adobe for close to $2 billion.

In this episode of How I Started, Connor Boyack sits down with John, an entrepreneur, CEO and Co-founder of ObservePoint, and a seasoned mentor to founders, to uncover the real story behind one of Utah's biggest tech success stories. They explore how John went from DJing church dances and shoveling fire pits to discovering an adjacent opportunity in website analytics to leading a company of over 1,200 employees.

Things You Will Learn

1. How to spot and act on adjacent opportunities that naturally grow out of the work you're already doing
2. How to choose a co-founder whose skill set complements yours and avoid the partnerships that fall apart
3. Why hyper-focusing on one thing early in a business create more success than chasing multiple ideas at once

Tools & Frameworks Covered

1. The Adjacent Possible: a method for recognizing and acting on business opportunities that emerge naturally from your current work and customer relationships
2. Bootstrapping as a Learning Tool: using lean, self-financed growth to stay close to your customer's real problems instead of spending your way past them
3. The Co-founder Compatibility Check: evaluating a potential business partner on complementary skills, shared ethics, and a clear wind-down agreement before committing

#HowIStarted #YouthEntrepreneurship #FounderJourneys #StartABusiness #Mentorship

Samantha White sits down with 12 year old Kyler Whaley, who sells at Indianapolis markets and has built a business around 3D printed products tailored to different audiences. He shares how he learned the business side of selling, from inventory and pricing sheets to customer conversation and market research, and why adapting to each event matters.

We discuss how Kyler chooses what to make, what sells best, and the lessons he has learned from selling in both kids markets and frequently speaking with adults.

Key topics:

• Market research
• Identifying top sellers
• Observing trends
• Learning skills behind the scenes
• The challenge of staying motivated

#3Dprinting #youngentrepreneur #kidsmarkets #IndianapolisMarkets #smallbusiness #marketresearch #customerpitching #inventorytracking #pricingsheets #fidgets #timemanagement #motivation #socialskills #productadaptation #audiencespecificproducts #familysupport

What if you never needed anyone's permission to start?

Zuby Udezue didn't wait, and the result was 30,000 albums sold hand-to-hand, across cities and countries, with no label, no manager, and no gatekeeper standing between him and his fans.

Zuby is a global rapper, author, and podcaster with millions of followers who built his entire career by going directly to his audience, starting with geo arbitrage as a teenager between Saudi Arabia and the UK, and scaling to a self-released music catalog, books, and a hit podcast.

In this episode, Connor and Zuby explore how founder journeys begin with a single bold move, why rejection is just the price of admission, and how the habits of early entrepreneurship compound into long-term success.

Things You Will Learn

1. How to identify a geo arbitrage opportunity and turn a personal advantage into your first sale
2. How to reframe rejection as a data point, and use it to sharpen your sales process over time
3. Why going direct to your audience, without gatekeepers, is a viable and powerful growth strategy at any age

Tools & Frameworks Covered

1. Geo Arbitrage: How to identify price gaps between markets and turn them into early-stage profit without upfront risk
2. Pre-Selling Before You Spend: How Zuby took orders before buying inventory, eliminating risk and proving demand first
3. The Rejection Reframe: A mindset method for tracking wins, ignoring losses, and building sales confidence through repetition

#YouthEntrepreneurship #FounderJourney #StartABusiness #Entrepreneurship #HowIStarted

In this episode of Startup Standouts, host Samantha White interviews 11-year-old Felicity Barbot, the founder of Girl Coded Boutique, a beauty product line focused on clean skincare for young girls.

Felicity shares her journey of starting her business, her experiences at various markets, and the challenges and successes she has faced. She emphasizes the importance of continual learning, customer engagement, and having a strong brand that draws people in.

Guest Links:

https://www.instagram.com/girlcodedboutique/

https://www.facebook.com/profile.php?id=61583418031281

Key topics:

• The importance of quality control and clean products
• Actively trying new things and learning from others at each market
• The joy of building a product you believe in and seeing others enjoy it as well

#youngentrepreneur #beautyproducts #cleanskincare #childrenentrepreneurship #marketexperiences #productdevelopment #businessadvice #socialmediamarketing

Most people assume great investors were born knowing how to build. Tim Draper's first business ended with a neighbor walking away with most of his earnings, and he still calls it one of the most formative moments of his life.

In this episode of How I Started, Connor Boyack sits down with Tim Draper, venture capitalist, founder of Draper University, and one of the most recognized names in global entrepreneurship, to trace the real origin of his founder mindset: from selling apples at the end of a quarter-mile driveway, to door-to-door oyster routes, to a Stanford-inspired board game written up in the Wall Street Journal.

Tim shares why failure in school is misunderstood, what traits he consistently sees in the entrepreneurs he invests in, and why the institutions dominating your parents' world are exactly the ones your generation is built to transform.

Things You Will Learn

1. How to reframe early failure as the most useful data a young entrepreneur can collect
2. What traits and habits Tim Draper consistently sees in the founders who go the distance
3. How to identify broken institutions and turn the problem into a real business opportunity

Tools & Frameworks Covered

1. The Five-Step Problem-to-Business Framework: Tim's sequential method for moving from frustration to fundable solution: identify the problem, solve it, build a business around it, monetize it, distribute it.
2. The TV Ad Signal: a practical filter for spotting industries ripe for disruption: if it's advertising heavily on television, it's likely providing a bad service at a high cost.
3. The Partner-First Approach to Early Ventures: Tim's method of building with collaborators from the start, so that failure becomes a shared learning experience rather than a solo setback.

#HowIStarted #YouthEntrepreneurship #FounderJourney #TimDraper #StartABusiness