Diners and Deals
Diners and Deals
Podcast Description
Welcome to Diners and Deals, the podcast where we dive deep into the journeys of entrepreneurs, business leaders, and investors making big moves in the business world. I’m your host, Seth, and in each episode, we bring you candid conversations with incredible guests who share their insights, successes, and the challenges they’ve faced along the way.
Whether it’s scaling a business, navigating private equity, or reinventing an industry, our guests bring a wealth of experience and a fresh perspective to the table. We go beyond the boardroom, discussing the personal stories and pivotal moments that have shaped their careers and the companies they’ve built.
Grab a coffee, pull up a chair, and join us as we talk shop in a casual, down-to-earth setting that feels more like catching up with old friends than a traditional business podcast. If you’re passionate about business, growth, and learning from those in the trenches, you’re in the right place. Welcome to Diners and Deals—let’s get into it!
Podcast Insights
Content Themes
The podcast covers themes such as entrepreneurship, scaling businesses, private equity, and industry innovation, with episodes discussing personal journeys like building a billion-dollar business, navigating equity investments, and transforming underperforming real estate.
Welcome to Diners and Deals, the podcast where we dive deep into the journeys of entrepreneurs, business leaders, and investors making big moves in the business world. I’m your host, Seth, and in each episode, we bring you candid conversations with incredible guests who share their insights, successes, and the challenges they’ve faced along the way.
Whether it’s scaling a business, navigating private equity, or reinventing an industry, our guests bring a wealth of experience and a fresh perspective to the table. We go beyond the boardroom, discussing the personal stories and pivotal moments that have shaped their careers and the companies they’ve built.
Grab a coffee, pull up a chair, and join us as we talk shop in a casual, down-to-earth setting that feels more like catching up with old friends than a traditional business podcast. If you’re passionate about business, growth, and learning from those in the trenches, you’re in the right place. Welcome to Diners and Deals—let’s get into it!
Rachel Saunders joins Seth Deutsch on Diners and Deals for a candid conversation about her unconventional path from big law to private equity to launching her own firm. She reflects on the mindset shift required to move from mitigating risk as a lawyer to taking risks as an entrepreneur, and how pivotal experiences—like investing in NFTs and running a crypto company—shaped her confidence to bet on herself. Rachel shares the lessons learned from building Saturday Legal, her vision for delivering legal services differently, and the personal values that guide her as a mother and founder.
We discuss:
* The transition from being “entrepreneurial” to fully embracing entrepreneurship
* Lessons from private equity and operating a crypto company through volatile markets
* The importance of taking personal risks to strengthen decision-making
* Building Saturday Legal on a flat-fee, client-first model instead of billable hours
* Balancing professional ambition with being fully present for family
This episode offers practical insight for anyone navigating career transitions, entrepreneurship, or redefining what success looks like on their own terms.
Links:
Saturday Legal – https://saturday-legal.com/
Rachel on LinkedIn – https://www.linkedin.com/in/rachel-b-saunders/
Seth on LinkedIn – https://www.linkedin.com/in/sethdeutsch/
Topics:
(00:00:00) – Intro (00:03:53) – Introducing Saturday Legal (00:05:36) – From entrepreneurial to entrepreneur (00:11:21) – Influences and upbringing (00:13:17) – Journey through education and early career (00:15:35) – Law school and early legal career (00:20:27) – Transition to Peak Six (00:26:16) – Learning to take risks (00:29:23) – The thrill of NBA Top Shot (00:30:37) – From investor to CEO: Embracing the unknown (00:31:06) – Navigating imposter syndrome (00:31:47) – The reality of operating a business (00:35:01) – The crypto company journey (00:39:48) – The decision to bet on myself (00:45:41) – The path to starting a law firm (00:56:13) – Balancing career and family (00:57:48) – Final thoughts and words of wisdom
Disclaimer
This podcast’s information is provided for general reference and was obtained from publicly accessible sources. The Podcast Collaborative neither produces nor verifies the content, accuracy, or suitability of this podcast. Views and opinions belong solely to the podcast creators and guests.
For a complete disclaimer, please see our Full Disclaimer on the archive page. The Podcast Collaborative bears no responsibility for the podcast’s themes, language, or overall content. Listener discretion is advised. Read our Terms of Use and Privacy Policy for more details.