Advertise on podcast: How I Started: Lessons from Entrepreneurs to the Next Generation

Addy is a young entrepreneur selling her decoupaged artwork out of Connecticut. She has a heart for inspiring smiles and joy in her customers, and accomplishes this in part by implementing a strategic “Pay What You Can” model. She sources her art supplies from low-cost places like thrift stores and the beach, and turns a profit that she reinvests back into her business. You won’t want to miss this episode! Guest Links: https://www.instagram.com/tideandtrinketbyaddy/ https://www.facebook.com/profile.php?id=61581617614450 Key topics: “Pay What You Can” pricing model Affordable sourcing Young business owners Business growth Decoupage artwork Confidence through entrepreneurship Building community in business Navigating business expenses #SmallBusiness #YoungEntrepreneurs #CraftBusiness #YouthEntrepreneurship #YoungArtist

What does it take to go from mowing lawns as a teenager to managing a $5 billion investment portfolio? Jeff Danley, Co-Founder and Managing Partner at Peak Capital, joins How I Started to walk through the full founder journey, from his first lawn-mowing business at 13 to building one of the early credit card review websites in the 1990s to becoming a seasoned investor backing entrepreneurs across Utah. Jeff shares why most of the best businesses start from a personal need, when it actually makes sense to raise funding, and why service-based side hustles are quietly among the strongest opportunities for young entrepreneurs right now. He also opens up about what investors really look for, why knowing your own goals matters more than chasing growth, and how creating jobs is one of the most meaningful outcomes of entrepreneurship. Things You Will Learn How to recognize a real business idea from your own life, and why the best founders start by solving a problem they personally have.When raising funding support helps your business grow, and when it can actually slow you down.Why service-based side hustles are one of the most overlooked opportunities for young entrepreneurs today.Tools & Frameworks Covered The Business Idea Book: Jeff's lifelong practice of writing down problems and ideas as he notices them, then researching which ones could become real businesses.The Default-No Funding Approach: a way of thinking about whether to raise capital, anchored in the principle that “70% of a big pie is better than 100% of a small pie.”the Service-Based Side Hustle Lens: a practical filter young entrepreneurs can use to spot underserved local needs and start a business with low competition. #FounderJourney #YouthEntrepreneurship #StartABusiness #SideHustles #Entrepreneurship

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 Why taking calculated risk is essential to entrepreneurship, and how Bill's higher tolerance for risk shaped six decades of real estate success.How to choose a business partner by looking at their values first, not just their resources or skills.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 The Contribution Mindset: reframing work and jobs as contributing to family, community, and country to build the foundation for future success.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.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 Youth entrepreneurshipStarting a handmade business as a childCrochet entrepreneurshipSelling at children’s entrepreneur marketsCreating unique productsProduct experimentation and innovationBuilding confidence through salesOvercoming fear and self-doubtHandling slow markets and bad weatherLearning from business setbacksProduct presentation and booth displaysUnderstanding customer behaviorFinding a target audienceSelling plushies and crocheted weaponsCustom orders and online sellingPersistence and not giving upTurning a hobby into a businessCreative problem-solvingThe 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 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 companyWhy rejection of your product is never a rejection of you and how understanding that difference unlocks the confidence to start sellingHow to discover what you're truly passionate about by noticing what makes people stop and listen when you speakTools & Frameworks Covered 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 marketsThe Passion Discovery Method: identifying your entrepreneurial niche by asking what topics make others lean in and keep listeningThe 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.comhttps://www.instagram.com/happyfacecreations24/https://www.etsy.com/shop/HappyFaceCreationKey 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 How to spot and act on adjacent opportunities that naturally grow out of the work you're already doingHow to choose a co-founder whose skill set complements yours and avoid the partnerships that fall apartWhy hyper-focusing on one thing early in a business create more success than chasing multiple ideas at onceTools & Frameworks Covered The Adjacent Possible: a method for recognizing and acting on business opportunities that emerge naturally from your current work and customer relationshipsBootstrapping as a Learning Tool: using lean, self-financed growth to stay close to your customer's real problems instead of spending your way past themThe 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 researchIdentifying top sellersObserving trendsLearning skills behind the scenesThe 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 How to identify a geo arbitrage opportunity and turn a personal advantage into your first saleHow to reframe rejection as a data point, and use it to sharpen your sales process over timeWhy going direct to your audience, without gatekeepers, is a viable and powerful growth strategy at any age Tools & Frameworks Covered Geo Arbitrage: How to identify price gaps between markets and turn them into early-stage profit without upfront riskPre-Selling Before You Spend: How Zuby took orders before buying inventory, eliminating risk and proving demand firstThe 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 productsActively trying new things and learning from others at each marketThe 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 How to reframe early failure as the most useful data a young entrepreneur can collectWhat traits and habits Tim Draper consistently sees in the founders who go the distanceHow to identify broken institutions and turn the problem into a real business opportunity Tools & Frameworks Covered 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.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.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

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 adaptingIncreasing in confidenceThe importance of free samples and bringing people into the boothPersistence is keyThe 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 How early curiosity and persistence can turn small hustles into big business success.Why adaptability and learning from mistakes is key to thriving in changing markets.How embracing emerging technologies, like AI, opens new opportunities for young entrepreneurs.Tools & Frameworks Covered Curiosity-Driven Learning – Teaches how to leverage observation and questioning for opportunities.Adaptability & Pivoting – Helps navigate changing industries and unexpected challenges.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 ageProduct testing and market adaptationCustomer engagement strategies #lawnmowing #smallbusiness #teenownedbusiness #youthentrepreneurship #3dprintingbusiness #kidsmarkets #businessgrowth #customerengagement #producttesting #entrepreneuriallessons