Teaching People to Lead: Turning High Performers Into Managers Who Thrive With Guest Ashley Fina, Co-CEO of Oxygen

Reinvention, AI, and the Art of Starting Over with Alexia Crawford, CEO of 8westervelt

Alexia Crawford has reinvented herself more times than most people get to try once. She moved to the U.S. at 19 with no work permit and started a jewelry business because it was the only option she had. That business eventually became a 55-location retail chain. Then came the bankruptcies, the burnout, and a single 11-hour seminar that changed everything. She is now CEO of 8westervelt, helping retail companies automate their operations, and she will tell you the 30 years of hard experience is the real product, not the technology. Rebecca Goodman-Stephens, CEO of Moses Singer [https://www.mosessinger.com] and host of “So Many Questions,” sat down with Alexia to talk through all of it, the chapters that were exciting, the ones that were brutal, and what she actually learned from each. They get into what it felt like to scale faster than her systems could support, how a difficult earn-out year changed the way she receives feedback, and how she ended up in an AI seminar that sent her life in a completely different direction. Alexia talks honestly about burnout, what caused it, what it cost her, and why she thinks it carried important lessons she needed she needed. She also makes a case that starting fresh, without legacy systems and entrenched ways of doing things, is one of the biggest advantages a company can have right now. If you have ever wondered what sustained reinvention actually feels like from the inside, this one is worth your time. In This Episode 01:35 — From Australia to New York 02:21 — The Barney’s Lesson 04:21 — Building Laila Row 09:48 — When Growth Outpaces Structure 12:07 — Having a Boss For the First Time 18:51 — Burnout 20:11 — Rebuilding Through YPO 21:43 — Discovering AI 24:52 — Full Automation in Practice 26:16 — Leading Without Certainty 37:07 — The Efficiency-First framework 39:56 — Advice to Entrepreneurs Guest Bio Alexia Crawford is CEO of 8westervelt [https://8westervelt.com/], an AI and automation company focused on retail operations. She spent more than three decades building businesses across jewelry manufacturing, wholesale, and retail before pivoting to AI. She is currently pursuing her MBA at NYU and has been a YPO member for 20 years. Relevant Links Moses Singer on LinkedIn [https://www.linkedin.com/company/moses-&-singer-llp/] Connect with Rebecca Goodman-Stephens on LinkedIn [https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/] YPO [https://www.ypo.org]

How Curious Leaders Build High-Growth Companies | Guest Katie Burke, Chief Operating Officer for Harvey

After 12 years helping HubSpot scale from 300 to 8,000 employees, Katie Burke joined Harvey [https://www.harvey.ai/] with one clear conviction: the key ingredient for scaling any company is humility. In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer [https://www.mosessinger.com], sits down with Katie Burke, chief operating officer of Harvey, to talk about what strong leadership actually requires when a company is growing fast and constantly evolving. Katie shares: * Why humility and curiosity matter more than a proven playbook * How Harvey’s hiring process is designed to talk candidates out of joining * What transparency should and should not include inside a growing organization * Why “Jobs Not Finished” is her favorite company value and what it looks like in practice * Why people management is something leaders have to relearn constantly If you lead a team in a fast-moving environment, this conversation is worth your time. Connect with Rebecca Goodman-Stephens on LinkedIn [https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/]

Building Cultures Where Risk-Taking Thrives | Guest Daniel Curtis, Chief Strategy Officer for emc3

What separates leaders who inspire bold thinking from those who quietly kill it? In this episode of So Many Questions, Moses Singer CEO and host Rebecca Goodman-Stephens sits down with Daniel Curtis, Chief Strategy Officer of global events agency emc3, for a conversation about fearless leadership, psychological safety, and the culture-building decisions that shape high-performing organizations. Daniel shares what it actually took to build a culture at emc3 where people feel safe taking risks and pushing creative boundaries. He talks about how four members of his leadership team publicly owned their biggest professional mistakes in front of the whole company, why he stepped out of his own role so a rising team member could take it, and what his move to New York signaled to the rest of the organization. He also walks through how emc3 built its values from the ground up, the non-negotiable behaviors baked into every onboarding, and why he believes culture without values is just background noise. Relevant Links Moses Singer [https://www.mosessinger.com] emc3 [https://emc3.com/] Connect with Rebecca Goodman-Stephens on LinkedIn [https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/]

Finding Your Leadership Style by Trusting Your Own Wiring | Guest Kara Brothers, Founder, New Juice Studios

What if the key to becoming a stronger leader isn’t changing yourself, but trusting how you’re wired? Kara Brothers, Founder of New Juice Studios, joins host Rebecca Goodman-Stephens to discuss building leadership confidence by understanding your natural style. Kara shares why it’s normal to question your worth in demanding environments, and how experience helps you separate “I’m not good enough” from “this isn’t the right fit.” Together, they discuss perspective-taking, quiet leadership, and how leaders can bring out the best in teams with different working styles. Links: www.mosessinger.com [https://www.mosessinger.com] Rebecca Goodman-Stephens on LinkedIn [https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/]

Leadership in the Future of Work with Guest Cindy Machles, Co-founder and CEO, Glue Advertising and Public Relations

Leadership today isn’t just about managing teams — it’s about designing how work gets done. Host Rebecca Goodman-Stephens, CEO of Moses Singer, speaks with Cindy Machles, Co-founder and CEO of Glue Advertising and Public Relations, about leadership in the future of work. They discuss how leaders can design organizations for flexibility, why courage and self-trust matter when making career-defining decisions, and how skills-based teams and technology are reshaping professional services. Links: Moses Singer: www.mosessinger.com [https://www.mosessinger.com] Glue Advertising and Public Relations: glueadvertising.com [https://glueadvertising.com/] Connect with host Rebecca Goodman-Stephens on LinkedIn [https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/]