
Agency Freedom
Agency Freedom Podcast exists to help insurance agency owners and sales professionals make the jump from the captive world to the independent side of the industry. We then equip you in every topic imaginable to help you dominate your market once you’re FREE. We deliver authentic, actionable and audacious content and hard-hitting interviews from the best former captives in the country. Make your Freedom Jump with Agency Freedom Podcast.
Latest episodes

Sep 29, 2023 • 28min
E122: IndieTech 2023 - AndDone Live
Recorded LIVE from IndieTech 2023!In this episode, James talks with Ryan Westerman, President of AndDone, and Chase Courtney, Director of Technology Sales at Imperial PFS.To learn more about AndDone, visit https://anddone.com/Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedomEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.Episode Highlights:
Chase and Ryan discuss AndDone, a wholly-owned subsidiary and payment solution that exists in the IPFS ecosystem, for the first time on a podcast. (3:59)
Ryan explains that AndDone is an API-first enterprise-grade payment solution application that offers a web app for agents to use. It is designed for integration with other solutions such as rate quote buying platforms and AMS systems. (12:34)
Chase mentions that IPFS has extensive experience in premium finance services and offers payment processing services to both customers and non-customers while prioritizing providing value and benefits to their customers without any extra charges. (16:30)
Ryan discusses the importance of selecting a solution that aligns with your business model and how your team interacts with customers and products. (19:58)
Ryan discusses the goal of IPFS which is to provide assistance and offer the most convenient and straightforward payment methods for insurance. (23:38)
Key Quotes:
“We're in the situation now, where we are replacing Stripe, we are replacing PayPal for our customers. No premium finance involved.” - Chase Courtney
“We wake up every day and have IPFS premium volume run through our payment processing. We pass those benefits on to our customers.” - Chase Courtney
“We want to give the easiest ways to pay. We want to give the simplest solution for you for the insurance and the options that you need to get that deal closed.” - Ryan Westerman

Sep 22, 2023 • 27min
E121: IndieTech 2023 - Hawksoft Live
Recorded LIVE from IndieTech 2023!In this episode, James talks with Paul Hawkins, CEO of Hawksoft & Jerry Fox, Vice President of Carrier Relations at HawkSoft.To learn more about HawkSoft, visit https://www.hawksoft.com/.Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedomEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.Episode Highlights:
Paul discusses how his son's passion for computers led to them to start Hawksoft. (2:26)
Jerry shares his role with Hawksoft and how he got involved with it. (5:41)
Paul shares his journey from working in a warehouse to digitizing insurance forms to building a thriving company. (9:25)
Paul explains that Hawksoft values relationships and choice, connecting with Insurtechs to provide independent agents with options for their unique businesses. (16:22)
Jerry mentions that Hawksoft's philosophy is centered around being a people-centric business, helping a people-centric industry protect the people and businesses around the country. (18:00)
Paul shares that their key to success is prioritizing relationships over finances, as it creates a sense of trust and support. (19:55)
Jerry discusses the unique company culture of Hawksoft where core values are not just talked about, but lived by the entire team, resulting in a dedicated and loyal workforce of 150+ employees. (21:47)
Key Quotes:
“The relationship is the top thing for us. When we bring on an agency to our system, they're part of the HawkSoft family.” - Paul Hawkins
“We are a people-centric business, helping a people-centric industry, protect the people and the businesses of the country.” - Jerry Fox
“My goal as a CEO is to raise up each one of my employees to become the best person that they can be both personally and professionally.” - Paul Hawkins

Sep 15, 2023 • 47min
E120: IndieTech 2023 - GloveBox Live
Recorded LIVE from IndieTech 2023!In this episode, James talks with Ryan Mathisen & Sean Mulhern, Co-Founders of GloveBox.To learn more about GloveBox, visit https://gloveboxapp.com/.Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedomEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.Episode Highlights:
Ryan mentions that this year GloveBox has successfully developed base features and is now focusing on releasing a desktop version and a metrics dashboard with policyholder analytics. (4:32)
Sean discusses his role as handling operations and being responsible for various tasks and processes within the company, including transitioning, executing, and strategizing for new features and go-to-market plans. (7:54)
Ryan shares that reflecting on past experiences and considering how to improve current processes is an invaluable tool for product development and workflow optimization. (16:40)
Sean discusses the importance of considering the prospect and aligning interests between the agency, policyholder, and carrier for successful interactions and benefits for all. (21:31)
Ryan explains the challenges of achieving SOC 2 compliance due to receiving data from multiple sources but highlights their efforts in strengthening security over the past two years. (24:40)
Ryan discusses the GloveBox app’s two agreements: one with the policyholder and one with the agency, allowing anyone to use the app and connect with carriers, while also enabling the sharing of policy information with agents. (29:31)
Ryan mentions that smaller agencies often prefer a simple and basic platform, so it's important to cater to their needs and facilitate the market accordingly. (34:16)
Ryan emphasizes the importance of being cautious about misinformation in the current tech-driven era and highlights the benefits of their platform for agents, which was built with the intention of improving their lives. (37:29)
Key Quotes:
“We're very excited about the desktop version. It's literally going to be this living, breathing client playground from your website. It's going to be awesome.” - Ryan Mathisen
“Think about your prospect. Think about the other person that you're talking to. And I think that's one thing we just inherently do really well at GloveBox is, every idea is filtered through a few different lenses… GloveBox, the policyholder, the agency, and the carrier. And it has to work for all of them.” - Sean Mulhern

Sep 8, 2023 • 23min
E119: IndieTech 2023 - Doug Mohr Live
Recorded LIVE from IndieTech 2023!In this episode, James talks with Doug Mohr, Vice President of Industry Relationships and Partnerships at Vertafore.To learn more about Vertafore, visit https://www.vertafore.com/.Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedomEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.

Sep 1, 2023 • 1h 4min
E118: Arel Moodie on Adult Development Theory
In this episode, James talks with Arel Moodie, Co-Founder of Talkadot.To learn more about Talkadot, visit https://www.talkadot.com/.Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedomEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.Episode Highlights:
Arel shares about his childhood growing up in a difficult environment and how his desire to get out of that environment fueled him. (2:53)
Arel discusses how he went from being a successful college student to hosting a TV show, getting invited to the White House, and standing on TEDx stages. (17:37)
Arel explains the conventional stages of adult development theory, including self-centric, group-centric, skill-centric, and achiever stages. (26:15)
Arel discusses how individuals move from a self-centric mindset to a group-centric one, where they accept the group's beliefs as their own and develop an "us versus them" mentality. (35:41)
Arel mentions the difference between the skill-centric and achiever stages, and how the latter involves enlisting people with complementary skills. (43:33)
Arel explains how the achiever stage involves delegating and empowering others, while the skill-centric stage tends to hold onto tasks and believe that nobody can do it as well as they can. (49:07)
Key Quote:“For any of us, when we look at our story, it's very easy to look at the things that happened to us and say, that's the exact reason why I can't make it. Where, I think if you look at it from a different perspective, you always build a skill set, you always build a survival mechanism to get through anything that's tough. And that mechanism, that skill might just be the thing that makes you more successful than you would have been without it.” - Arel Moodie

Aug 25, 2023 • 54min
E117: Tomer Kashi On Skywatching Over Your Clients
In this episode, James and guest host Peter talk with Tomer Kashi, Co-Founder & CEO of VOOM Insurance and SkyWatch.To learn more about VOOM Insurance, visit https://www.voominsurance.com/.Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedoEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.Episode Highlights:
Tomer explains how his company, VOOM Insurance, and InsurTech MGA that creates usage-based insurance products for underserved niche segments within the mobility world. (4:24)
Tomer discusses his education and background in the Israeli army, which led him to become a tech founder in the insurance industry. (7:52)
Tomer shares the founding story of SkyWatch and how it started as a commercial drone insurance solution. (13:03)
Tomer explains how SkyWatch expanded into other niche insurance segments, such as motorcycle insurance, and the advantages of a pay-per-mile basis. (19:50)
Tomer explains how SkyWatch prices its drone insurance policies based on utilization and offers an optional telematics service to provide a risk score. (26:21)
Tomer mentions that drone insurance is currently a product that is pulled by commercial drone operators and their customers, rather than pushed by brokers and that it is not yet necessary for generalist agencies to offer it across the board. (34:05)
Tomer explains that SkyWatch works with aggregators like First Connect for distribution, but also offers direct appointments for those with relevant customers. (41:23)
Tomer shares their teamwork within the company, with a core value of "It's never not my problem." (47:02)
Key Quotes:
“Skywatch started as a commercial drone insurance solution. You see drones everywhere, from wedding photographers, to drone deliveries and in agriculture inspection. Really, everyone like even doing live shows, and we have customers in all of these segments.” - Tomer Kash
“We need to help these newcomers to join the industry,. We also see ourselves as a part of the ecosystem that wants to help this industry to thrive because we're, you know, benefiting from that. So, we work with flight schools, and we work with other organizations to promote flight safety, and also, you know, promote insurance.” - Tomer Kash
“One of the core values of our company is, “It's never not my problem”. Meaning, the R&D really cares about what the sales are doing in a day to day, and vice versa, and marketing and compliance everything. Really, everyone walks together. And this is what really drives everyone to work every day. It goes through different time zones, which is not easy.” - Tomer Kash

Aug 18, 2023 • 40min
E116: Fly On The Wall In A Hard Market Conversation
In this episode, you get to listen in to a private shop talk conversation James had with a group of agency principal in Somewhere, USA.Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedomEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.Episode Highlights:
A speaker on the call shares the importance of integrating core values into daily activities and operations, particularly in the context of trucking and sales. (5:16)
James discusses the possibility of charging a fee in addition to the commission, the requirements for different licenses, and the potential profitability of running their own insurance program as both a wholesaler and retailer. (13:29)
James discusses his struggle with holding people accountable and his growth as a leader by delegating responsibilities to others, in order to focus on his own growth and goals. (18:51)
A speaker on the call discusses their profitable focus on personal lines and plans to expand into commercial lines while delegating day-to-day operations to managers. (24:21)
James explains the importance of narrowing down the target market and specializing in a specific niche to gain a competitive advantage and better serve clients. (26:33)
A speaker on the call emphasizes the importance of prioritizing qualifying needs and diving deeper into the process while acknowledging that there is no wrong process as long as there is a process in place. (32:53)
A speaker on the call mentions that James is known for executing his business strategies, making him a standout among others who only talk about it. (33:43)
A speaker on the call believes that joining a call with other independent agents can be beneficial for personal growth and motivation. (34:15)
Key Quote:“You have to give your team opportunity to fail and fail big. That's the only way you grow. Otherwise, you're rate limited. You're capped. ” - James Jenkins

Aug 11, 2023 • 14min
E115: Strong Opinions About The Hard Market
In the final installment of our summer solo episode series, James talks about navigating the hard market.Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedomEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.

Aug 4, 2023 • 26min
E114: Hot Takes and Strong Opinions (Part 3)
In this episode, James talks about 4 reasons why you should NOT launch an insurance-related podcast in 2023.He ends the episode with a much better idea for generating real impact and profitable opportunities for your office.Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedomEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.

Jul 28, 2023 • 23min
E113: Hot Takes And Strong Opinions (Part 2)
This is the second installment of hot takes and strong opinions, James talks about prospecting and how to better connect with new prospects in the sales process.Visit our website to join our email list, get the scoop on our LIVE coaching calls and never miss an episode: https://www.agencyfreedom.comConnect with Agency Freedom Podcast on Facebook at the Agency Freedom Podcast group: https://www.facebook.com/groups/agencyfreedomEmail us at podcast@agencyfreedom.com with ideas, questions, complaints or your favorite grilling recipe.