Ashley Bright is a former advertising creative director turned entrepreneur and co-founder of Makertank, a platform designed to help founders build sustainable businesses with the right systems and support.
After spending 15 years in the agency world working with major brands like Microsoft and Amazon, Ashley began to question the traditional path of success, especially after a pivotal career setback and the perspective shift that came with becoming a parent. That turning point led to a deeper exploration of storytelling, communication, and ultimately entrepreneurship, where Ashley has spent over a decade navigating the highs and lows of building a business.
In this conversation, Ashley shares honest insights on identity, emotional intelligence, and what it really takes to move from external success to meaningful, self-directed work.
IN THIS EPISODE YOU'LL LEARN:
00:35 – Ashley shares how an early love for storytelling began as a teenager, obsessing over commercials and recorded clips before having the language to define it.
01:42 – Reflects on choosing advertising as a “safe path” instead of pursuing film, despite wanting to become a director.
07:51 – Identifies “creative director” as the pinnacle role, associating it with success, leadership, and creative control.
09:10 – Shares the reality of leadership: more bureaucracy, egos, and management, pulling focus away from creative work.
10:10 – Despite promotions and financial success, each step forward quietly chipped away at curiosity and fulfillment.
13:23 – Becoming a parent begins to shift perspective, prompting deeper reflection on purpose, legacy, and priorities.
15:23 – Recounts being “thrown under the bus” at work, a turning point that forced a reevaluation of career direction.
19:11 – Describes this moment as a catalyst, alongside discovering teaching and new possibilities outside traditional roles.
24:08 – Shares a defining lesson: “Don’t listen to what people are saying, listen to what’s motivating what they’re saying.”
26:17 – Explains a shift in perspective, moving from surface-level reactions to understanding underlying emotions and motivations.
32:27 – Emphasizes that awareness and presence are the first steps toward emotional intelligence and better decision-making.
35:40 – Highlights entrepreneurship as both challenging and transformative, requiring resilience, self-trust, and growth.
39:47 – Admits that many struggles came from not asking for help and lacking awareness early on.
41:28 – Describes the shift from isolation to connection, where vulnerability and support began to change everything.
45:09 – Explains the cycle many entrepreneurs fall into: short-term wins followed by setbacks, without building true momentum.
47:04 – Michael introduces the concept of “scaffolding,” emphasizing the need for systems beyond just skill or talent.
47:56 – Introduces Makertank, built to give entrepreneurs structure, support, and a better way to grow.
50:57 – Makertank combines AI-powered tools, community, and resources to help founders focus on high-value work.
54:20 – Raises a key question: how do you take your value from within a company and turn it into something you own?
55:41 – Highlights identity as one of the biggest challenges when transitioning from corporate roles to entrepreneurship.
59:52 – Compares Makertank to a personal trainer, focused on accountability, progress, and real results.
01:03:22 – Shares that even highly successful people experience imposter syndrome, reinforcing that everyone struggles.
01:06:39 – Uses a metaphor of water finding its path, emphasizing trust in the process and growth over time.
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BOOKS AND RESOURCES
- Brené Brown (author and researcher on vulnerability, identity, and emotional intelligence)
- Alan Watts (philosopher known for teachings on presence, life perspective, and Eastern philosophy)
- American History Tellers (podcast series that explores historical events through storytelling)
- Makertank website
- Connect with Ashely on LinkedIn.
