ABOUT THIS PODCAST 🔗

Update frequency:
weekly
Average audio length:
16 minutes
Guest interviews
English
United States
90 episodes
since Sept. 26, 2025
episodic

LATEST EPISODE 🔗

Gabby Stoller joined Walmart's food team when it was 20 people and left after it grew past 400. Then she walked away from Fortune 1 for a 100 person ad tech company, a move plenty of people told her was bonkers. At Big Happy she built a digital out of home business on tech the company owns, turning…

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PREVIOUS EPISODES

I handed Tim Kilroy my website and asked him to rip it apart, and he did. Live, line by line. Tim's been scaling agencies since 2001, and this teardown exposes the trap almost every expert falls into: making your whole site about you instead of answering the only two questions a visitor actually as…
"Are you a high-income professional worried about a $20-a-month tool outsmarting your PhD? In this episode of Simple Wins, we dive into how B2B AI growth can give you godlike powers to turn your vision into reality. We explore why you simply cannot delegate AI implementation to others and why maste…
Are you worried that a $20-a-month subscription is about to replace your entire creative firm? In this episode, we dive into the future of creative agency growth and why the rise of automation is actually a massive opportunity for elite practitioners. As AI creates a ""sea of sameness"" in the mark…
Are you struggling to keep up with customer demands while trying to scale your business? In this episode, we dive into how AI team members are revolutionizing the front office for entrepreneurs everywhere. We sit down with Coach Carroll to discuss the rapid shift in technology and why small busine…
Are you tired of feeling like you are hiking with a backpack full of rocks while trying to scale your company? In this episode of Simple Wins, we explore the stages of growth and how to identify the hidden barriers to growth that keep most B2B firms stuck for years. Many founders find themselves tr…
Are you tired of being viewed as just another untrustworthy salesperson? In this episode of Simple Wins, we dive into the art of relationship building and why authenticity is your greatest competitive advantage in today's market. If you want to scale your business, you have to stop leaning on being…
Are you struggling with acquisition turbulence or a team that isn't pulling in the same direction? In this episode of Simple Wins, we explore how to achieve internal alignment so your business can scale without the friction of mixed messages. Many B2B founders focus solely on the ""cover of the boo…
Are you stuck in the hustle phase, working for a business that owns you instead of the other way around? In this episode, we explore how to build a value creation business that generates true wealth and freedom. Scaling a business requires a radical shift from constant grinding to building autonomo…
Are you frustrated that your latest tech investments aren't moving the needle? In this episode of Simple Wins, we tackle the massive hurdle of AI implementation and why a staggering 95% of B2B firms fail to see a real return on their investment. Most leaders get distracted by the noise, but the sec…
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