Ask Ashley is a monthly podcast produced by Montgomery Entertainment LLC (ME), a boutique events agency based in the San Francisco Bay Area. CEO Ashley Montgomery and her team invite you to join their discussion on various creatively curated themes related to business, finance, leadership, entrepreneurship, and more!
AI is everywhere, but how do we use it without losing our human touch?
In this episode of Ask Ashley, digital marketing strategist Maddie Smiley joins Ashley Montgomery to unpack the evolving role of AI in both work and daily life. From managing client expectations in a fast-moving industry to outsourcing meal planning with ChatGPT, Maddie shares a refreshingly honest take on where AI helps—and where it still falls short.
25 Mar 2025
Laughing Through Life
In this episode of Ask Ashley, we sit down with comedian Jeff Applebaum to talk about the power of humor, his journey in stand-up comedy, and the unexpected lessons he's learned along the way.
7 Mar 2025
Elevating Customer Success
In this Ask Ashley episode, we explore the world of Customer Success—what it really means, why it’s crucial for business growth, and how to build lasting relationships that drive retention.
28 Jan 2025
Thriving in the Remote Work Era
In this episode of Ask Ashley, we dive into the evolving world of remote work and share strategies to help you thrive. From boosting productivity and building meaningful connections to enhancing collaboration and maintaining a healthy work-life balance, Ashley and Jack explore practical tips and insights for success in the remote era.
This podcast is an extension of Montgomery Entertainment, LLC. For more, visit montgomeryentertainment.net. (montgomeryentertainment.net)
17 Dec 2024
Mastering Sales Development: Part 3
Sales development expert Sean shares actionable insights on effective onboarding, training, and compensation strategies to boost sales team performance and drive revenue growth.
28 Nov 2024
Mastering Sales Development: Part 2
Sean shares actionable insights on mastering outreach strategies, leveraging AI tools effectively, and setting your team up for long-term sales success.
30 Oct 2024
Mastering Sales Development: Part 1
On this episode of Ask Ashley, we dive into the world of sales development with Sean, a seasoned expert in building high-performance sales teams and effective strategies. Sean shares insights on structuring a successful sales development process, the qualities to look for when hiring top talent, and how to evaluate candidates for long-term success. We also explore how AI is reshaping prospecting and what sales teams can do to stay ahead in an evolving landscape. Whether you’re a sales professional or a business leader, this episode is packed with actionable tips to boost your sales strategy!
This podcast is an extension of the Montgomery Entertainment, LLC brand. For more, visit montgomeryentertainment.net.
25 Sept 2024
Mastering Event Registration: Insights with Michael
In this episode of Ask Ashley, we sit down with Michael, a seasoned events and registration expert. Michael shares his journey from the hospitality industry to becoming a freelance event professional. We dive into the intricacies of event registration, including platform selection, managing client expectations, and streamlining processes for large and small events. Michael also shares valuable insights on optimizing attendee experiences and engaging them from the moment they arrive. Tune in to learn key tips for successful event registration and management!
This podcast is an extension of the Montgomery Entertainment LLC brand. For more, visit montgomeryentertainment.net.
16 Jul 2024
Mastering Sales Leadership
In the latest episode of Ask Ashley, Kevin Mulrane delves into the intricacies of effective sales leadership, sharing strategies to unlock a team's full potential. He emphasizes the crucial role of a good manager in driving success and fostering growth among sales professionals. Listeners will gain valuable insights into enhancing their leadership skills and achieving outstanding results.
This podcast is an extension of the Montgomery Entertainment LLC brand. For more, visit montgomeryentertainment.net.
12 Jun 2024
Empowering Your Safety
In this episode of Ask Ashley, Ashley speaks to James Hamilton, a nationally recognized personal security expert and former FBI agent. Listen to this episode to learn about how to establish top-notch security not only in events but also in your personal life!
This podcast is an extension of the Montgomery Entertainment LLC brand. For more, visit montgomeryentertainment.net.
8 May 2024
San Francisco Renaissance??
In this episode of Ask Ashley, Ashley catches up with long-time colleague and friend, Alex Tourk as they talk about his business in San Francisco!
This podcast is an extension of the Montgomery Entertainment LLC brand. For more, visit montgomeryentertainment.net.
2 Apr 2024
Meet the Podfather
In this episode of Ask Ashley, Ashley chats with craft chocolate expert and "chocolate sourcerer" Greg D'Alesandre about his career, recent travels, the upcoming Craft Chocolate Experience, and more!
This podcast is an extension of the Montgomery Entertainment LLC brand. For more, visit montgomeryentertainment.net.
26 Mar 2024
Mastering Sales Partnerships
In this episode of Ask Ashley, Ashley chats with Poya Osgouei! The two chat about client relationships, the sales process, and adapting to market changes in event sponsorships.
This podcast is an extension of the Montgomery Entertainment LLC brand. For more, visit montgomeryentertainment.net.
23 Jan 2024
What You Didn’t Know About Alison
In this episode of Ask Ashley, Ashley interviews her sister and photographer Alison Smiley, owner of Alison Smiley Photography! Alison has been an event photographer since 2013 and has a passion for creating images that tell a story and document heartfelt emotion and human connection. She has been described by clients as being able to effortlessly capture natural smiles and personalities, in a very relaxed and fun way. Detail-oriented and organized, those who work with her are also quick to point out her thorough and easy communication style. Find out what brought her to where she is today, and what working on events with Ashley is like!
This podcast is an extension of the Montgomery Entertainment LLC brand. For more, visit montgomeryentertainment.net.
12 Jul 2023
Ask Ashley Trailer
The Ask Ashley podcast, hosted by Ashley, is an engaging and informative show available on Spotify. It explores a wide range of topics related to business, leadership, finance, entrepreneurship, and more. The podcast invites listeners to ask questions and seek advice on various aspects of professional growth and success. Through engaging conversations, expert interviews, and practical tips, Ashley aims to inspire and empower individuals in their professional journeys. Whether you're a budding entrepreneur, a seasoned executive, or simply looking to level up your professional game, Ask Ashley provides valuable insights and strategies to help you thrive in the fast-paced world of business.
This podcast is an extension of the Montgomery Entertainment LLC brand. For podcast updates and episodes go to our website, Spotify, or Apple Podcasts.
28 Jun 2023
Life in Sales with Bryan Elsesser
In this episode of "Ask Ashley," Ashley interviews Bryan Elsesser, the managing director of Elsesser Ventures and her new sales and partnership lead for The ME Collective. Bryan shares his career journey, from early sales experiences to becoming an accomplished sales and partnerships lead. They discuss how his diverse interests and ventures, like being a volunteer firefighter, real estate broker, and opera singer, contribute to his success in sales. They explore the inspiration behind starting Elsesser Ventures and driving growth for SaaS and service businesses. Bryan provides valuable insights into event sales, sales and marketing dynamics, strategies for success, industry changes, universal principles for companies, overcoming challenges, emerging trends, and advice for aspiring sales professionals.
27 Apr 2023
Diversity & Inclusion with Walker Williams
In this episode of Ask Ashley, we are joined by inclusion and autism advocate, Walker Williams, to discuss the importance of creating an inclusive environment where everyone feels like they belong. As April is Autism Awareness and Acceptance month, Walker shares his experiences as an autistic individual and how being open and vulnerable with his colleagues at The Walt Disney Company has empowered him to be a better cast member. We explore the challenges of fostering inclusivity and the role that empathy and understanding play in building a diverse and equitable workplace or community. Join us for an inspiring conversation on doing right by people in life and business.
5 Mar 2023
Fear in Life and Business with Braelin Thornton</a#x3E;
Braelin Thornton is a financial advisor with Thornton Wealth Management. Braelin has been a part of Ashley’s personal advisory board for a little over five years. Recently Ashley sat down with expert Braelin for a Q&A to give our audience insight and advice on all things fear, money, business, and life.
For more, visit montgomeryentertainment.net.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
98
Score snapshot 15 Sept 2025
Apple Podcasts (US)
5.0 / 5
1 ratings
Spotify
5.0 / 5
1 ratings
Podcast Authority Score: 33 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
29
Social presence
0
YouTube
63
Engagement
32
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