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
21 Aug 2025TRANSCRIPT
From Immigrant Grit to Transforming the Law Firm Model - Andy Kvesic - CEO of Aprio Legal
Host Seth Deutsch interviews Aprio Legal CEO Andy Kvesic about his immigrant roots, entrepreneurial journey, and innovative approach to transforming the law firm model.
19 Jun 2025TRANSCRIPT
From Chaos to Clarity: Building Enduring Service Businesses - John Barrett - Executive Director at ISSA
Executive Director John Barrett at ISSA discusses building enduring service businesses with host Seth Deutsch, sharing insights on resilience, humility, and curiosity in this interview.
15 May 2025TRANSCRIPT
From Stuntman to Service Empire: Building with Grit and Purpose - Josh Zolin - CEO of Windy City Equipment
Host Seth Deutsch interviews Josh Zolin, CEO of Windy City Equipment, about building a purpose-driven service empire from a stuntman's grit.
17 Apr 2025TRANSCRIPT
The Investrepreneur Model: Marrying Vision with Execution - Scott Silverman - Founder and CEO of Agman
Host Seth Deutsch interviews Scott Silverman, Founder and CEO of Agman, about his "Investrepreneur" model for building enduring companies in overlooked sectors.
27 Mar 2025TRANSCRIPT
Creating Long-Term Value in Niche Markets Through Operational Excellence - Dave Rauch - CEO @ ProTec
Host Seth Deutsch interviews Dave Rauch, CEO of ProTec, about building long-term value in niche HOA markets through operational excellence and preventive maintenance.
20 Feb 2025
Operational Agility: Pioneering Private Equity through Human Capital - Matt Schachman - Co-Founder - Cold Bore Capital
Host Seth Deutsch interviews Matt Schachman, Co-Founder of Cold Bore Capital, discussing operational agility and human capital's role in private equity buy-and-build strategies.
16 Jan 2025
Building a Billion Dollar Business in 3 Years - Steve Carroll - CEO of Kelso Industries
Host Seth Deutsch interviews Steve Carroll, CEO of Kelso Industries, about building a billion-dollar business through strategic acquisitions and effective finance management.
19 Dec 2024
Serial Entrepreneurship and What it Means to Take Ownership of a Business - Matt Matros - Founder and GP at NCC
Seth Deutsch interviews serial entrepreneur Matt Matros, Founder and GP at NCC, about taking ownership and succeeding in the #1 seat of a business.
21 Nov 2024
Frank Campise - Co-Founder and Principal of Jab Real Estate
Host Seth Deutsch interviews Frank Campise, Co-Founder and Principal of Jab Real Estate, about building a successful real estate company and navigating the future market.
17 Oct 2024
Navigating Growth and Private Equity: Reid Lappin and Henry Byrne on Scaling Vokal in the Digital Age
Host Seth Deutsch interviews Vokal Founder & CEO Reid Lappin and CFO Henry Byrne about scaling Vokal through organic and inorganic growth strategies.
26 Sept 2024
Building a Restoration Empire: Chris Santiago on Scaling, Operations, and Culture in the Lower Mid-Market
Chris Santiago is the CEO of RUI Construction. RUI provides multi-state construction services such as emergency restoration, fire reconstruction, fire and smoke damage repair, flood damage, water mitigation, structure drying, renovations, and additions.
A Great Range Capital portfolio company since January 2022, the mid-market company is currently expanding nationally through de novo growth strategies and synergistic acquisition opportunities.
On this episode, Seth and Chris discuss:
Implementing technology into RUI
Building out the CFO office
Making the transition to the middle-markets
& much more!
Links:
Chris Santiago on LinkedIn (https://www.linkedin.com/in/chrisasantiago/)
RUI Construction (https://repairs-unlimited.com/)
Seth Deutsch on LinkedIn (https://www.linkedin.com/in/sethdeutsch/)
Great Range Capital (https://greatrangecapital.com/)
Topics:
(00:00:00) - Intro
(00:03:42) - Chris’ career and company
(00:06:47) - background and upbringing
(00:11:39) - Making the jump from big corporate to the lower mid-market PE world
(00:21:00) - Chris’ first year in the restoration business
(00:27:34) - Learning the levers of the business and industry
(00:30:14) - Implementing technology into the business
(00:41:08) - Building out the CFO office
(00:46:44) - What to look for in a business partner and CFO
(00:48:41) - Predictions for the restoration industry
(00:52:28) - What should folks be asking themselves if they want to make the transition that you have to the lower middle-markets?
This Podcast is brought to you by CSuite Financial Partners.
11 Sept 2024
Welcome to Diners and Deals
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!
[…] I am trying to deliver legal services differently than a traditional law firm would because I think there's a big gap in the market. I think that the billable hour is pretty broken, especially with... the increasing use of AI in the delivery of legal services. And so I have a model where I just charge clients a flat monthly fee and I'm basically retained and I do a whole range of different tasks for my clients to help them just move their business forward. Sometimes it's legal, sometimes it's not, sometimes it's legal adjacent, but they're looking for someone who can kind of act like a concierge counsel to them I was going to say, it sounds like concierge medicine to me. […]
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