So Many Questions

Moses Singer
  • 5.0 (2)
  • Business

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.

Episodes

  1. Jul 9

    How Leaders Build Trust and Create Lasting Impact with Michael Luongo, Owner, Evolve Athletic Club

    What does it take to build trust with the people you lead, and make it last? In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, talks with Michael Luongo, owner of Evolve Athletic Club, where he trains CEOs, entrepreneurs, and high-performing professionals. Michael shares how a simple first conversation can become the foundation of a real working relationship, how pushing past his discomfort with outreach changed the trajectory of his business, and what he's observed about the leaders who grow the fastest. Relevant Links Moses Singer Evolve Athletic Club Connect with Rebecca Goodman-Stephens on LinkedIn

  2. Jun 4

    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

  3. May 14

    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, 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

  4. Apr 9

    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 emc3 Connect with Rebecca Goodman-Stephens on LinkedIn

  5. Mar 4

    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 Rebecca Goodman-Stephens on LinkedIn

  6. Feb 5

    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 Glue Advertising and Public Relations: glueadvertising.com Connect with host Rebecca Goodman-Stephens on LinkedIn

  7. Jan 7

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

    Moses Singer CEO Rebecca Goodman-Stephens speaks with Oxygen co-CEO Ashley Fina about what it truly takes to develop strong leaders, and the systems today’s managers need to perform at their best. In this Discussion  00:29 – Guest introduction  01:53 – Becoming CEO at 25  06:36 – Coaching and leadership development  08:33 – The leadership skills gap  12:55 – Coachability and values alignment  15:33 – Turning values into behaviors  20:30 – Navigating family business dynamics  23:18 – Partner selection and expectations  27:30 – Strength of community and learning  29:24 – Why asking for help matters   Links Moses Singer Website: www.mosessinger.com Oxygen Website: https://www.leadwithoxygen.com/ Connect with Rebecca Goodman-Stephens on LinkedIn: https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/ Learn more about Oxygen and leadership development with Ashley Fina: https://www.leadwithoxygen.com/

  8. 12/03/2025

    Leading With Vulnerability with Guest Lindsi Shine, CEO of Insider NYC

    Lindsi Shine, CEO of INsider NYC, discusses what it means to lead with vulnerability. Her and host Rebecca Goodman-Stephens explore how balancing strength with openness shapes leadership, builds trust, and creates resilient workplace cultures. Key Timecodes: 00:28 – Guest Introduction 01:00 – The Heart of Lifestyle Management 03:16 – Valuing Vendors Like Family 09:13 – Showing Up With What You’ve Got 10:54 – Leading Through Personal Crisis 13:06 – Vulnerability as a Leadership Strength 15:15 – Building a Team Culture of Tenacity 19:30 – Prioritizing Team Needs in Business Decisions 21:39 – Coexisting Opposites in Leadership 26:12 – Extending Empathy Beyond Business 31:41 – Final Reflection: Advice to Her Younger Self Links: Moses Singer: www.mosessinger.com INsider NYC: www.insidernyc.com Rebecca Goodman-Stephens on LinkedIn: https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/

  9. 11/13/2025

    Culture and Leadership in Professional Services with Guest Shireen Hilal, CEO of Maior Consultants

    In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, speaks with Shireen Hilal, CEO of Maior Consultants, about culture and leadership in professional services. They explore how empowering people, building trust, and shaping authentic culture drives firm performance and client success. Key Timecodes 00:28 – Guest Introduction 01:18 – Career Journey: From Law to Consulting 07:06 – Thought Leadership as a Growth Strategy 10:22 – Obsess About Clients, Not Competitors 14:41 – Leadership Traits that Drive Change 19:59 – Dream Clients and Long-Term Engagements 24:11 – Alternative Fee Arrangements 27:23 – Innovation in Mid-Sized Firms 29:06 – Advice for Managing Partners 32:36 – Building Engaged, Empowered Teams 36:31 – Business Development Success Stories 42:55 – Leadership Lessons for Her Younger Self Moses Singer: www.mosessinger.com Maior Consultants: https://www.maiorconsultants.com/ Rebecca Goodman-Stephens on LinkedIn: https://www.linkedin.com/in/rebecca-goodman-stephens-b702665/

  10. 10/16/2025

    Breaking Barriers and Building Impact with Guest Jacqueline Newman, Managing Partner of Berkman Bottger Newman & Schein, LLP

    In this episode of So Many Questions, host Rebecca Goodman-Stephens, CEO of Moses Singer, speaks with Jacqueline Newman, Managing Partner of Berkman Bottger Newman & Schein, LLP, about women leading change in law and the power of building impact beyond the practice. They explore her journey as a leader in a male-dominated industry, the creation of the 2181 Group to accelerate gender parity in law, and her philanthropic projects including the Gift of Giving Store for domestic violence shelters and the entrepreneurial venture Muffin Crumbles. Episode Timeline and Highlights: (00:00) Intro & podcast mission (00:29) Introduction: Jacqueline and Rebecca’s kickoff (00:45) Jacqueline’s early inspiration & law interest (01:12) Unexpected path to matrimonial law (03:32) First job in matrimonial practice (04:18) Evolving role into leadership & partnership (06:04) Defining firm culture & intentional leadership (08:21) Culture rituals: surprise events, spa, scavenger hunts (11:59) Hiring: "Will you annoy me?" and people fit (13:35) Introducing the Culture Index tool (17:30) Giving back: Gift of Giving Store (pop-ups in shelters) (22:52) The “Muffin Crumbles” venture with her daughter (26:32) Vision for growth: preserving relationships and culture (29:44) Milestone “gifts to myself” & setting boundaries (33:40) Women in leadership & launching the 2181 Group (38:49) Advice to younger self: relax, have fun, smile (39:45) Closing remarks & podcast outro Learn More Moses Singer: www.mosessinger.com Berkman Bottger Newman & Schein, LLP: https://www.berkbot.com Rebecca Goodman-Stephens on LinkedIn If this conversation resonated: Subscribe to So Many Questions so you never miss an episode Share this episode with a colleague or friend Leave a review / rating on Apple Podcasts, Spotify, or your favorite app

  • 10 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

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.

Information

  • Creator
    Moses Singer
  • Years Active
    2025 - 2026
  • Episodes
    10
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    So Many Questions

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