Wish you could get in the head of an effective business leader? Host Rebecca Goodman Stephens, a law firm CEO who trained in clinical and organizational psychology, does just that on her podcast. Each episode, she interviews leaders across industries who share real stories of success. So Many Questions features authentic, fun, and insightful conversations that reveal what it really takes to lead in business.
Connecting the Dots: How Curiosity Built a Nonlinear Career With Marci Weisler, Managing Director of Oaklins DeSilva+Phillips
How does a winding career commercializing emerging technology lead to M&A? In this episode of So Many Questions, host Rebecca Goodman-Stephens sits down with Marci Weisler, Managing Director of Business Development at Oaklins DeSilva+Phillips.
3 Sept 2026
How to Move Fast When You Can’t Afford to Be Wrong with Rawia Ashraf, Head of Product, CoCounsel Transactional & GCOs at Thomson Reuters
Rawia Ashraf, Head of Product for CoCounsel Transactional & GCOs at Thomson Reuters, discusses her journey from Big Law attorney at Simpson Thacher to product leader, sharing insights on building AI tools for legal professionals and managing high-stakes product development.
6 Aug 2026
How Your Leadership Style Lands on Your Team with Steven Lerche, President of Goldstar Jewellery
How does an optimistic leader avoid burning out the team around them?
Steven Lerche, President of Goldstar Jewellery, joins host Rebecca Goodman-Stephens, CEO of Moses Singer, to talk about leading a large, multigenerational business through pressure and constant change.
Steven explains how his instinct toward optimism shapes his leadership, and why he leans on methodical people to balance his big-picture thinking. Rebecca, who admits her own version can tip into toxic positivity, digs into the friction that shows up when a leader hands off tasks without explaining the reasoning behind them, and why a colleague who pushes back is usually trying to help an idea succeed, not block it.
The conversation moves into leading through real pressure: commodity swings, a 56% tariff that forced Goldstar to open a new factory within 90 days, and where AI is actually useful in the business. Steven also shares the fear he considers the biggest of his life.
In This Episode
01:14 – The scale of the business Steven leads05:24 – Employee tenure and company culture08:07 – Optimism as a leadership style10:01 – Objections as a sign of investment11:08 – Delegating without full context14:28 – Responding to the tariff crisis17:39 – A therapy concept for business crises19:28 – Rethinking the interview process22:45 – Balancing fatherhood and business25:30 – The fear of the second generation
Relevant Links
Moses Singer: www.mosessinger.com
Goldstar Jewellery: www.goldstarjewellery.com
Connect with Rebecca Goodman-Stephens on LinkedIn: https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/
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9 Jul 2026
How Leaders Build Trust and Create Lasting Impact with Michael Luongo, Owner, Evolve Athletic Club
Building real trust with the people you lead starts long before any big moment. It starts with how you show up in the small ones.
In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, sits down with Michael Luongo, owner of Evolve Athletic Club, about what it takes to lead in a way that lasts.
Michael shares how he turns an intake conversation into the foundation of a lasting relationship, what finally pushed him to get comfortable with outreach, and what he’s noticed about the leaders who grow the fastest in his gym.
4 Jun 2026
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 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, 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
Connect with Rebecca Goodman-Stephens on LinkedIn
YPO
14 May 2026
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 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, speaks with Katie Burke, chief operating officer of Harvey, about what strong leadership actually requires when a company is growing fast.
9 Apr 2026
Building Cultures Where Risk-Taking Thrives | Guest Daniel Curtis, Chief Strategy Officer for emc3
Building a culture where people feel safe taking risks is harder than it sounds. In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, sits down with Daniel Curtis, Chief Strategy Officer of global events agency emc3, to talk about what fearless leadership actually looks like in practice.
Daniel shares what his leadership team did to build an environment where creativity and calculated risk-taking are expected, not just tolerated. He talks about the moment four leaders stood up in front of the whole company to share their biggest professional mistakes, why he stepped aside so a rising team member could take over his role, and what his move to New York in his 40s signaled to the organization. It is a candid, practical conversation about psychological safety, values-driven culture, and the leadership behaviors that make bold teams possible.
4 Mar 2026
Finding Your Leadership Style by Trusting Your Own Wiring | Guest Kara Brothers, Founder, New Juice Studios
What if leadership growth starts with trusting your own wiring? Kara Brothers, Founder of New Juice Studios, joins the show to discuss finding your leadership style by understanding what comes naturally, and stopping the reflex to reshape yourself to fit someone else’s model.
Kara and host Rebecca Goodman-Stephens explore why self-doubt often shows up when the environment is a mismatch, and how perspective-taking and observation can be leadership strengths, not liabilities.
5 Feb 2026
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.
7 Jan 2026
Teaching People to Lead: Turning High Performers Into Managers Who Thrive With Guest Ashley Fina, Co-CEO of Oxygen
Rebecca Goodman-Stephens, CEO of Moses Singer, speaks with Ashley Fina, co-CEO of Oxygen, about what it truly takes to develop great leaders. They explore why so many high performers struggle when promoted into management, how culture and clear expectations shape leadership behaviors, and what skills and support systems today’s managers need to lead teams and navigate constant change successfully.
3 Dec 2025
Leading With Vulnerability with Guest Lindsi Shine, CEO of Insider NYC
Lindsi Shine, CEO of Insider NYC joins host Rebecca Goodman-Stephens for an honest and emotional conversation about what it means to lead with vulnerability. They explore how strength and openness can coexist in leadership, and how authenticity and emotional intelligence create resilient teams and lasting business relationships.
13 Nov 2025
Culture and Leadership in Professional Services with Guest Shireen Hilal, CEO of Maior Consultants
Host Rebecca Goodman-Stephens, CEO at Moses Singer, speaks with Shireen Hilal, CEO of Maior Consultants, about culture and leadership in professional services. They explore how giving employees a real voice shapes authentic culture, how trust fuels client and team engagement, and the leadership lessons needed for firms to thrive.
16 Oct 2025
Breaking Barriers and Building Impact with Guest Jacqueline Newman, Managing Partner of Berkman Bottger Newman & Schein, LLP
Rebecca Goodman-Stephens, CEO of Moses Singer, speaks with Jacqueline Newman, Managing Partner of Berkman Bottger Newman & Schein, LLP, about women breaking barriers in the legal profession and creating impact beyond the practice. They explore her leadership journey, the founding of the 2181 Group for women managing partners, and her initiatives like the Gift of Giving Store and Muffin Crumbles. Together, they share lessons on building purposeful leadership and driving change inside and outside the workplace.
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2 ratings
Spotify
5.0 / 5
1 ratings
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