How I Started: Lessons from Entrepreneurs to the Next Generation

Most people only see the highlight reel but every lasting career is built in the quiet, unseen moments. In this episode of How It Started, Connor Boyack speaks with Mike Tannenbaum, former NFL General Manager, ESPN analyst, and founder of The 33rd Team, about the long road behind his career in professional sports. Mike shares how working for free, saying yes to unglamorous roles, and focusing on service shaped his path from intern to executive. They talk about building trust, creating value in any role, and why progress comes from committing to the process rather than chasing quick wins. This conversation offers clear lessons for anyone starting out, especially those learning how small decisions add up over time.Things You Will LearnHow to make yourself useful before you have influence or authorityHow to build relationships without making them transactionalWhy focusing on process builds confidence, resilience, and momentum Tools & FrameworkValue-First Approach – Serving before expecting resultsRelationship-Building vs. Transactional Thinking – Creating trust instead of asking for favorsListening as Leverage – Using attention and curiosity to stand out#Resilience #LeadershipLessons #HowItStarted #ValueCreation #PersonalGrowth

Aiden Easterwood and his siblings have cracked the code when it comes to maximizing profit and standing out from the competition. Aiden talks about their growth from a single 3D printer and modest profits, to a home buzzing with printer noise and bringing in hundreds of dollars. Instagram - https://www.instagram.com/3deepdesigns/Key topics:Starting a business at a young ageBuilding confidence through salesSibling teamwork in businessMarketing and customer engagementLessons learned from market experiencesGuest links:https://www.instagram.com/3deepdesigns/#kidsentrepreneurship #marketselling #businesslessons #confidencebuilding #siblingteamwork #caramelapples #youthbusinesssuccess #3Dprinting

What if a single late-night moment could quietly shape the rest of your life?In this episode, Russell Brunson shares the unexpected spark that first pulled him into entrepreneurship at just 12 years old and how that curiosity evolved into a lifelong obsession with understanding how businesses grow. Russell Brunson, entrepreneur, author, and founder of ClickFunnels, walks Connor Boyack through his earliest ventures, the lessons hidden in infomercials and junk mail, and how reverse-engineering successful businesses became the foundation of his philosophy. Listeners will gain a grounded perspective on learning by observation, avoiding modern entrepreneurial traps, and building valuable skills in a rapidly changing, AI-driven world.Things You Will LearnHow early exposure to business models can shape long-term entrepreneurial thinkingWhy modeling proven success often beats starting from scratchHow young entrepreneurs can avoid common traps in today’s oversaturated online economyTools & FrameworksFunnel Hacking – Reverse-engineering successful businesses to shorten the learning curveSkill-Stacking Strategy – Focusing on one valuable skill before building a full businessModeling vs. Copying – Learning structure without unethical imitation#Entrepreneurship #BusinessMindset #CreatorEconomy #DigitalBusiness #StartupStories

Capri Fife started going to the markets when they first launched in Salt Lake City. What began as a family tradition of making caramel apples turned into a profitable business when she was just 9 years old. Now, a college student 10 years later, she reflects on her experiences selling apples and working with her sister.Instagram - https://www.instagram.com/annmarieapples/Key topics:Starting a business at a young ageBuilding confidence through salesSibling teamwork in businessMarketing and customer engagementLessons learned from market experiencesGuest links:Instagram - https://www.instagram.com/annmarieapples/#KidsEntrepreneurship #MarketSelling #BusinessLessons #ConfidenceBuilding #SiblingTeamwork #CaramelApples #YouthBusinessSuccess

What if the biggest advantage in entrepreneurship isn’t money, connections, or credentials but curiosity and the courage to question the rules?In this episode, Connor Boyack sits down with Matt Higgins, co-founder of RSE Ventures, Shark Tank guest investor, bestselling author of ‘Burn the Boats’, and fellow at Harvard Business School, to talk through the moments that shaped his path from growing up in poverty in Queens to building a life centered on freedom and ownership. Matt reflects on his earliest business attempts, the lessons he learned from necessity, and how curiosity, confidence, and persistence played a role at every stage. The conversation explores how ideas are formed through lived experience, why imposter syndrome shows up even at the highest levels, and how young founders can build momentum by focusing on the next right decision.Things You Will LearnHow to cultivate curiosity and confidence to fuel entrepreneurial success.Why making yourself indispensable early in any role accelerates opportunity.How to spot proprietary insights and turn them into profitable ventures.Tools & Frameworks CoveredProprietary Insights Framework – Identify unique business opportunities based on personal experience.Freedom-Focused Decision Making – Prioritize autonomy to guide long-term business choices.Modern Entrepreneurial Tools – Using AI and digital platforms to test and launch low-cost ventures.#Entrepreneurship #FounderJourney #StartupLessons #ConfidenceBuilding #HowIStarted

In this introductory episode of Startup Standouts, host Samantha White introduces the series focused on young entrepreneurs participating in Kids Markets. She emphasizes the mission of Kids Markets to empower children aged 5 to 17 by providing them with real business experiences. Samantha highlights the impact of the unique stories these young entrepreneurs will share. We will get a look into the challenges they face and the growth they experience, particularly in their confidence and real-world skills. Both young, older, established, or aspiring entrepreneurs can be inspired by the incredible journeys of these kids. Key topics:Starting a business at a young ageBuilding confidence through salesSibling teamwork in businessMarketing and customer engagementLessons learned from market experiencesGuest links:Instagram - https://www.instagram.com/annmarieapples/#KidsMarkets #YoungEntrepreneurs #EntrepreneurialSpirit #Confidence #BusinessSkills #StartupStories #ChildrensMarkets #Empowerment #FinancialLiteracy #PersonalGrowth

Most people believe entrepreneurship starts with a business. This episode proves it starts with a mindset.In the inaugural episode of How It Started, host Connor Boyack, President of Kids Markets, breaks down why entrepreneurship is not about owning a company but about critical thinking, problem solving, and creating value in every role of life. Connor shares the story behind launching a nationwide movement that allows kids ages 5–17 to start real businesses, the legislation that made it possible, and the powerful lessons young people learn when they are trusted to build, fail, and grow.Listeners will gain a new understanding of what it truly means to think and act entrepreneurially, and how that shift can transform families, education, and the next generation of leaders.Things You Will LearnHow children can develop entrepreneurial skills early in life.The impact of real-world learning on problem-solving and critical thinking.How mentorship and structured programs can accelerate entrepreneurial growth.Tools & Frameworks CoveredKids Markets - Enables kids to sell real products and earn money.Youth-friendly business legislation - Lowers barriers for minors starting businesses.Youth Market Framework - teaches kids to launch real products for real customers#YouthEntrepreneurship #KidsBusiness #EntrepreneurMindset #MentorshipMatters #HowIStartedPodcast

How I Started is a podcast about the real journeys behind entrepreneurship, from the first idea to decades of impact.  Hosted by Connor Boyack, author of the Tuttle Twins children's book series, the show brings together seasoned founders who built remarkable companies and young entrepreneurs taking their first steps into business. Through honest conversations about risk, mistakes, pivots, mentorship, and growth, listeners hear what it actually takes to build something meaningful.  The show explores the full arc of entrepreneurship. Some episodes feature experienced founders sharing lessons from building companies over decades. Others spotlight middle school, high school, and young adult entrepreneurs launching their very first ventures. Together, these stories show that entrepreneurship can start at any age.  How I Started exists to inspire the next generation of builders and to connect them with the people who want to support them. For young listeners, the show makes entrepreneurship feel achievable. For successful founders and supporters, it highlights the impact of mentorship, resources, and funding on young entrepreneurs.  If you believe the next great businesses can start in a classroom, a garage, or a side hustle, this podcast is for you.