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PODCAST · business

Ask Ashley

by Maddie Smiley

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!

Publisher-supplied feed metadata · PodParley refreshed Jun 18, 2025 · Source feed

Episodes

  1. The Real Role of AI in Marketing (and Life)

    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...

  2. 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.

  3. 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.

  4. 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...

  5. Mastering Sales Development: Part 3

    In Part 3 of our conversation with Sean, we wrap up our discussion on everything sales development! 🚀 The two discuss the importance of onboarding and training, and compensation strategies for sales teams. This podcast is an extension of the Montgomery Entertainment, LLC brand. For more, visit...

  6. Mastering Sales Development: Part 2

    In Part 2 of our conversation with Sean, we dive even deeper into the world of sales development! 🚀 Sean shares actionable insights on mastering outreach strategies, leveraging AI tools effectively, and setting your team up for long-term success. Whether you’re leading a team or just starting in...

  7. 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,...

  8. 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…

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  9. 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…

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  10. 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...

  11. 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.

  12. 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...

  13. 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.

  14. 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…

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  15. 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...

  16. 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...

  17. 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...

  18. 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…

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ABOUT THIS SHOW

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!

HOSTED BY

Maddie Smiley

Frequently Asked Questions

How many episodes does Ask Ashley have?

Ask Ashley currently has 18 episodes available on PodParley. New episodes are automatically indexed when they're published to the podcast feed.

What is Ask Ashley about?

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,...

How often does Ask Ashley release new episodes?

Ask Ashley has 18 episodes. Check the episode list to see recent publication dates and frequency.

Where can I listen to Ask Ashley?

You can listen to Ask Ashley on PodParley by clicking any episode. We provide an embedded audio player for direct listening, and you can also subscribe via your preferred podcast app using the RSS feed.

Who hosts Ask Ashley?

Ask Ashley is created and hosted by Maddie Smiley.
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