How I Started: Lessons from Entrepreneurs to the Next Generation

How Christina Tosi Started and Grew Milk Bar

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

Turning Passion and Perseverance into Profits: The Vintage Violet

Kenzleigh Reed-Wynn goes into depth about her journey with her small business, The Vintage Violet. Kenzleigh shares the heart and story behind her unique offerings, including build-your-own bouquets, homemade sugar scrubs, and simmer pots. Her challenges, accomplishments, and stories from the markets make for an excellent listen for entrepreneurs of all ages. Guest Links: https://www.instagram.com/kenz.thevintageviolet/ Key topics: * Selling make your own bouquets * Turning personal restrictions into product ideas * Young entrepreneurship * Facing weather challenges * Overcoming shy tendencies #youthentrepreneurship #kidsmarkets #flowerbusiness #youngentrepreneur #smallbusiness #handmadeproducts #marketchallenges #personalgrowth #adviceforkids #floralarrangements

The Career Journey of Mike Tannenbaum, Former NFL General Manager

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 Learn * How to make yourself useful before you have influence or authority * How to build relationships without making them transactional * Why focusing on process builds confidence, resilience, and momentum Tools & Framework * Value-First Approach – Serving before expecting results * Relationship-Building vs. Transactional Thinking – Creating trust instead of asking for favors * Listening as Leverage – Using attention and curiosity to stand out #Resilience #LeadershipLessons #HowItStarted #ValueCreation #PersonalGrowth

Standing Out from the Crowd: 3Deep Prints

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 age * Building confidence through sales * Sibling teamwork in business * Marketing and customer engagement * Lessons learned from market experiences Guest links: https://www.instagram.com/3deepdesigns/ #kidsentrepreneurship #marketselling #businesslessons #confidencebuilding #siblingteamwork #caramelapples #youthbusinesssuccess #3Dprinting

How Russell Brunson Started and Grew ClickFunnels

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 Learn * How early exposure to business models can shape long-term entrepreneurial thinking * Why modeling proven success often beats starting from scratch * How young entrepreneurs can avoid common traps in today’s oversaturated online economy Tools & Frameworks * Funnel Hacking – Reverse-engineering successful businesses to shorten the learning curve * Skill-Stacking Strategy – Focusing on one valuable skill before building a full business * Modeling vs. Copying – Learning structure without unethical imitation #Entrepreneurship #BusinessMindset #CreatorEconomy #DigitalBusiness #StartupStories