How I Started: Lessons from Entrepreneurs to the Next Generation

The Career Journey of Mike Tannenbaum, Former NFL General Manager

21 min · 6. maj 2026
episode The Career Journey of Mike Tannenbaum, Former NFL General Manager cover

Description

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

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16 episodes

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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

1. juli 202623 min
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24. juni 202613 min
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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

17. juni 202630 min
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