Meet Evan O'Donnell an early-stage investor + co-founder of the VC firm, Timespan.

Evan shares his powerful journey of overcoming the deep-seated fears instilled from growing up closeted as a gay man, striving for perfection to avoid the perceived catastrophe of being outed. Through self-work, Evan shed the limiting armor he had built up and transformed his heightened perception from a self-protective mechanism into a "superpower" for intuition, creativity, and problem-solving.

By continuously confronting his fears, he has found a way to unlock new possibilities for personal growth and professional success.

Host Angie D'sa, Talentism coach + partner, highlights how fear so often limits leaders' ability to learn and unleash their unique potential. In conversation with Evan, Angie learns:

• How pursuing entrepreneurship felt scary -> "it's the purest form of self-actualization”
• How his armor still showed up at work, even after he came out
• How he methodically grapples with fear when it shows up at work
• How this deepens trust with his co-founder and they make better decisions as a result
• How his “super perception” drives faster feedback loops and better business outcomes

If you want to learn more about the framework Angie references in this episode, check out Purpose in the Big 4 model.

Meet Meghan Joyce the founder + CEO of Duckbill, an AI-and-human powered answer to tiresome but deeply necessary life admin - think renewing your passport or making appointments with doctors who actually take your insurance.

But MJ wasn't always "Founder or Bust." In fact, she has spent most of her career working for pretty iconoclastic founders. First at the ride-sharing app Uber, then at the health insurance provider Oscar. In this episode, MJ vividly describes what it felt like to be baffled or upset by her boss’s behavior. And admits she now sees herself doing some of those same baffling things as founder and CEO! As Joni Mitchell might put it, she’s looked at life from both sides now.

Her executive coach of over 11 years, Libbie Thacker (coach + partner at Talentism), has been with her through all the ups and downs and joins us as well. Listen as MJ brings rare insight into how bosses and employees so often miss each other and what to do about it.

Meet Ope Bukola. She’s founder and CEO of Kibo School, an online university in Africa.

Ope is both relatable and remarkable. Relatable because, like so many founders, at one point she looked around her company and felt a pang of disappointment - everyone was falling short of her expectations. Remarkable because, instead of blaming her team, she did the uncomfortable thing and asked how she was contributing to that dynamic.

She realized she was giving her people lots of autonomy - the thing she most craved. But she was failing to give them what they needed. This included clarifying her expectations, driving alignment around a problem statement, and giving regular feedback.

In this episode, you also get to hear from Ope’s coach Mandisa Khanna! Mandisa helped untangle Ope’s frustration and helped her acknowledge a blindspot: because Ope thrived in ambiguity, she was blind to the structure that others on her team might need.

With Mandisa’s support, Ope experimented with new and sometimes unnatural behaviors. Eventually, Ope learned that managing her team more closely (the thing she silently dreaded) actually unlocked a way more entrepreneurial culture (the thing she wanted most). When people understood what she wanted, they were more creative, risk-taking, and agile.

If you’ve ever thought, “Do I have to fire everybody?” Ope shares an inspiring alternative.

Favorite moments of the episode:

• 5:04 Ope “hits a management wall”. She cancels 1:1s with direct reports when she sees the agendas (they were supposed to populate) are empty!

• 11:04 Ope realizes that by not making her expectations explicit and known, she is making it virtually impossible for her direct reports to meet those expectations

• 16:27 Ope accepts that sharing her expectations and offering up frameworks and guiding principles are critical elements to managing well at Kibo

• 19:48 Mandisa shares how Ope's talent for structured thinking and strong goal orientation feeds into a "talent blindspot" (Ope underestimates how distinct and rare that talent / distinction truly is)

• 27:16 Mandisa and Ope describe what it feels like to design & run experiments squarely inside your blindspot and how Ope applied her structured, methodical approach to this challenge. Angie references Mandisa’s article “Escaping the Feedback Loop” (4 min read)

• 34:39 “What she was actually afraid of didn't come true.” Mandisa and Ope reflect that investing more into management, allowed for more autonomy and creativity from the team and cultivated a culture of learning that Ope deeply craved for Kibo.

To learn more about how Talentism works with leaders like Ope, visit www.talentism.com