Best Olivia Watson Podcasts (2024)

1
#72 - Business Partnerships: Lessons Learned w/ Grant Weber 35:56

3h ago35:56

35:56

In this episode Carey and Lindsay sit down with Grant Weber, President of TruSummit Insurance Solutions to talk about the entrepreneurship, partnerships, and the challenges of business ownership. Grant shares his personal experiences and lessons learned, offering valuable advice for those considering partnerships. He emphasizes the importance of cl…

1
The First Customer - Top Notch Personal Branding and Operations Mastery with COO Alyson Caffrey 24:02

2d ago24:02

24:02

In this episode, I was lucky enough to interview Alyson Caffrey, the dynamic COO of Operations Agency. Alyson recounts her East Coast upbringing and how the "Northeast hustle" instilled a unique drive in her. Despite not coming from an entrepreneurial background, she became an "accidental entrepreneur" after leaving her 9-to-5 job. Within 30 days o…

1
#71 - Could Data Change the Acquisition Space w/ David Watson 37:37

3d ago37:37

37:37

In this episode, Carey and Lindsay are joined by David Watson from RiskAdvisor to talk about the impact of data on agency operations and acquisitions. The conversation covers the topic of RiskAdvisor's functionality, and explores the efficiency and value of capturing and leveraging data, as well as the potential for data-driven decision-making in a…

1
The First Customer - The Strategic Ascent from Air Force to Tech with CPO and CTO Jeremy Gordon 26:11

4d ago26:11

26:11

In this episode, I was lucky enough to interview Jeremy Gordon, CPO and CTO of Startup Science. Jeremy shared his background, revealing how his experience with the Air Force laid the groundwork for his disciplined and focused approach to entrepreneurship. He spoke about his transition from military life to civilian pursuits, including his ventures …

1
The First Customer - The unconventional roadmap to being a serial entrepreneur with Founder AJ Bruno 42:13

10d ago42:13

42:13

This episode is extra special because I was lucky enough to interview THE AJ Bruno, Founder and CEO of QuotaPath. AJ wears many hats—he's a limited partner, podcast host, serial entrepreneur, commercial pilot, dad, and much more! AJ delves into the personal aspects of his life, including his upbringing in Pittsburgh, where his father's entrepreneur…

1
#70 - Launching Trusted Risk Advisor Status 33:54

10d ago33:54

33:54

In this episode, Lindsay and Carey sit down with Elliot Bassett, the president of Ellerbrock-Norris and co-founder of Rocketship Ventures. They discuss Elliot's journey in the insurance industry and the development of Launch, a software platform designed to help insurance agencies become trusted advisors to their clients providing a roadmap to assi…

1
Our Bound Liberation - Episode 1.03 - Marcia Lee 1:14:14

20d ago1:14:14

1:14:14

From the creators of Kultivating Kapwa Our Bound Liberation: Conversations in the time of Decolonization - Episode 1.03 In this episode of Our Bound Liberation, we are joined by Marcia Lee. We discuss asking the right questions, what it means to be our own one true love, what it means to connect, and more. Marcia Lee is committed to finding joy in …

1
#69 - Embracing Vulnerability and Authenticity w/ Meg McKeen 36:27

19d ago36:27

36:27

In this episode, Lindsay and Carey are joined by Meg McKean to discuss imposter syndrome, knowing your worth, and redefining success. They explore the challenges and doubts that come with pursuing a non-traditional career path, the importance of embracing your own journey, and the power of vulnerability and authenticity. Meg shares her own experien…

1
The First Customer - Transforming Business through Compassionate Leadership with Jerry Macnamara 26:08

18d ago26:08

26:08

In this episode, I was lucky enough to interview Jerry Macnamara, CEO and Founder of Proven Chaos. Jerry grew up just outside of Philadelphia and his entrepreneurial spirit wasn't directly influenced by his parents but rather by his high school soccer coach. Inspired by his frustration as a senior leader making others rich with his decisions, he de…

1
Our Bound Liberation - Episode 1.02 - Hāwane Rios 1:07:12

28d ago1:07:12

1:07:12

From the creators of Kultivating Kapwa Our Bound Liberation: Conversations in the time of Decolonization - Episode 1.02 "I stand ...in the sovereignty of my body ...in the sovereignty of my land ...with you in sacred solidarity" In this episode of Our Bound Liberation, we are joined by Hāwane Rios. We discuss sovereignty of the body, sovereignty of…

1
#68 - Family First w/ Olivia Schmitt 33:09

26d ago33:09

33:09

In this episode, Lindsay and Carey sit down with Olivia Schmitt from Vertafore to talk about personal and professional growth in the insurance industry. Covering various topics, including their love for family and dogs, the importance of having a mentor, and redefining success in different areas of life. Olivia shares her experience transitioning f…

1
The First Customer - Serial Entrepreneur Masterclass with 4x Founder Matt Watson 23:54

25d ago23:54

23:54

In this episode, I was lucky enough to interview Matt Watson, Founder, CEO, and CTO of Full Scale. Matt grew up around entrepreneurial parents who ran a flea market business, he gained early exposure to the world of business and sales. His first venture, Venn Solutions, stemmed from a serendipitous encounter with a car dealer needing software assis…

1
#67 - Investing in the Right Tools w/ Kevin Panter 37:16

1M ago37:16

37:16

In this episode, Lindsay and Carey sit down with Kevin Panter, the owner of Kevin Panter Insurance and a founding member of Southeastern Network Agencies (SNA) to discuss the importance of technology and learning from failure. Kevin emphasizes the importance of hiring the right people, partnering with the right companies, and investing in technolog…

1
The First Customer - From Dot-com bubble burst to successful digital agency with Adam Trachtman 28:52

1M ago28:52

28:52

In this episode, I was lucky enough to interview Adam Trachtman, Director and Owner of Lucid Circus. Adam's upbringing in Haverford, Pennsylvania, and his formative years at a creative and performing arts high school in Philadelphia laid the groundwork for his journey. With a blend of analytical precision inherited from his mother and a risk-taking…

1
Our Bound Liberation - Episode 1.01 - Davidica Little Spotted Horse 1:18:24

1M ago1:18:24

1:18:24

From the creators of Kultivating Kapwa Our Bound Liberation: Conversations in the time of Decolonization - Episode 1.01 "Diversify Tactics: Bringing Our Whole Selves to the Movement" In this episode of Our Bound Liberation, we are joined by Davidica Little Spotted Horse. We discuss having pride in who you are, staying focused when fighting for what…

1
#66 - A Lawyers Take on The FTC Non-Competes Ban w/ Jennifer Weaver 42:36

1M ago42:36

42:36

In this episode, Carey and Lindsay sit down with Jennifer Weaver, a lawyer at Manning Fulton & Skinner, P.A., who specializes in insurance industry litigation, to discuss the recent ruling by the FTC banning non-compete clauses in employment contracts. She explains that non-competes are agreements between employers and employees that prevent the em…

1
The First Customer - Startup and Franchising magic with Karim Kerachni 29:44

1M ago29:44

29:44

In this episode, I was lucky enough to interview Karim Kerachni, Co-founder of Steamates and head of franchise development for Massachusetts at PropertyGuys.com. Karim shares insights into his entrepreneurial journey and unique approach to productivity while traveling the world. Born in Canada and raised in France, Karim's upbringing in a family of…

1
#65 - Playing the Long Game w/ Jimi Honochick 32:53

2M ago32:53

32:53

In this episode, Carey and Lindsay sit down with Jimi Honachek, Vice President of YMI Insurance, to talk about his industry journey. From integrating into his family agency's legacy to fostering trust among the staff, Jimi shares invaluable insights reflecting on his podcasts for local marketing initiatives, and the intricacies of implementing tran…

1
The First Customer - The proven strategies of CEO Whitney Stowell in building a sales pipeline 23:20

2M ago23:20

23:20

In this episode, I was lucky enough to interview Whitney Stowell, Founder and CEO of Cribworks. Whitney discusses his entrepreneurial journey from a rural upbringing to navigating the fast-paced business world. Growing up on a farm instilled an entrepreneurial spirit in Whitney, who later transitioned into the professional realm by working in gover…

1
#64 - From Doctor to Insurance Agent w/ Jacob Eisenrich 35:02

2M ago35:02

35:02

In this episode, Lindsay and Carey interview Jacob Eisenrich, Vice President of Weatherby-Eisenrich Insurance. Jacob shares his unique background as a doctor who transitioned to the insurance industry and discusses the reasons for leaving the medical field and how he settled on insurance as a career. Jacob emphasizes the importance of being data-dr…

1
The First Customer - Leveraging Systems and Automation to Scale Profitably with CEO Olivia Parkes 23:22

2M ago23:22

23:22

In this episode, I was lucky enough to interview Olivia Parkes, CEO of The Systems Boss. Olivia shares her story of moving from the UK to Chicago, driven by a desire to pursue her dreams and create a thriving enterprise in the United States. From her early aspirations to her eventual realization of starting her own company, Olivia's tale is one of …

1
#63 - The Truth about Selling Your Agency w/ Matt Naimoli 35:04

2M ago35:04

35:04

In this episode, Lindsay and Carey sit down with Matt Naimoli to discuss Matt's journey of selling his agency. They cover topics such as finding the right partner, educating oneself on the selling process, and setting expectations for the future. Matt shares his insights on running the business with a future sale in mind and the significance of day…

1
The First Customer - How to build a world-class legal firm with Iterative Improvements 31:16

2M ago31:16

31:16

In this episode, I was lucky enough to interview Rachel King, CEO and Founder of King Law Firm. Rachel offers insights into her journey as an entrepreneur and lawyer. Her upbringing, shaped by divorced parents and small business owners in the family, instilled in her a passion for law and entrepreneurship. Her father's profession as a lawyer and ex…

1
#62 - Marketing 101 w/ Daniel Smith 36:54

2M ago36:54

36:54

In this episode, Lindsay and Carey interview Daniel Smith, the co-founder of Market Retrievers, a digital marketing agency for insurance agencies. They discuss the importance of marketing for agencies and provide insights on how to effectively market insurance services. They cover topics such as choosing the right marketing channels, utilizing AI i…

1
The First Customer - How to Disrupt and Improve Contact Centers with CloudWave CEO Mike Powrie 25:02

2M ago25:02

25:02

In this episode, I was lucky enough to interview Mike Powrie, CEO and Founder of CloudWave. Mike delves into the genesis and evolution of CloudWave as a disruptive force in the contact center industry. Mike's background in IT, particularly in unified communication, laid the groundwork for his entrepreneurial journey. CloudWave was born out of frust…

1
#61 - In Memory of Bobby Salmon 40:48

2M ago40:48

40:48

🕊 In Memory of Bobby Salmon 🕊 In this special re-launch episode, we pay tribute to our Bobby Salmon, whose passion in the independent insurance industry continues to inspire us. Join Carey and Lindsay as they revisit their conversation with Bobby, delving into the importance of fostering relationships in our industry and shaping its future. Though …

1
The First Customer - Fostering Education: A Spectacular Approach to Literacy with Adrian Knight 27:50

3M ago27:50

27:50

In this episode, I was lucky enough to interview Adrian Knight, CEO and Founder of Spectacular Group. Adrian delves into his journey as an acquisition entrepreneur and his unique approach to business. A World Champion participant in the Spartan games, Adrian shares his experiences and insights into building successful ventures. Adrian's entrepreneu…

1
#60 - Reflecting on Failures w/ Chris Paradiso 44:11

3M ago44:11

44:11

In this episode, Carey and Lindsay sit down with Chris Paradiso, the owner of Paradiso Insurance. They discuss Chris's background in insurance and the importance of discipline and mental readiness when buying an agency. Chris shares his experiences with failure and the lessons he has learned from them. He emphasizes the significance of building rel…

1
The First Customer - How to redefine partnership dynamics with Crossbeam CEO Bob Moore 38:17

3M ago38:17

38:17

In this episode, I was lucky enough to interview Bob Moore, CEO and co-founder of Crossbeam, a leading company in the partnership intelligence space. Bob shares his journey, emphasizing his passion for solving the challenges of partnership growth, which led to the inception of Crossbeam. He delves into the essence of Crossbeam, portraying it as a d…

1
The First Customer - Building a brand by betting on yourself with the Hey Jay Founder Jasmin Alić 40:02

3M ago40:02

40:02

In this episode, I was lucky enough to interview The Jasmin Alić, Founder of Hey Jay, and also a LinkedIn aficionado. Jasmin dives deep into his journey, starting with his childhood in war-torn Bosnia. Despite the adversity, Jasmin found solace in American hip-hop, which sparked his love for English and writing. Initially aspiring to be a rapper, J…

1
The First Customer - Charting the Techscape with Capablanca Co-Founder Luis Castaneda 25:27

3M ago25:27

25:27

In this episode, I was lucky enough to interview Luis Castaneda, co-founder and CTO of Capablanca. Luis dives into his journey from growing up during the emergence of the internet to his current role in the tech space. Luis shares how his early experiences with DIY computing in a culture of innovation laid the foundation for his career in technolog…

1
#59 - Owning Your Niche w/ Clinton Orr 33:12

3M ago33:12

33:12

In this episode, Carey and Lindsay sit down with Clinton Orr, an insurance agent and partner at iProtect Insurance. Clinton shares his journey in the insurance industry, starting from his background in real estate and his transition to insurance. He discusses the importance of finding a niche and building a book of business, particularly in the com…

1
The First Customer - Unfolding The Gentleman's Formula with Tiege Hanley CEO Kelley Thornton 30:31

3M ago30:31

30:31

In this episode, I was lucky enough to interview Kelley Thornton, CEO and Founder of Tiege Hanley. Kelley's inspiration for Tiege Hanley stems from his personal experience and observation of the skincare market's untapped potential in the United States. Initially, he sought to cater to older demographics like himself but found unexpected success am…

1
The First Customer - Transforming Customer Experiences Through Impactful Alliances with Lamees Butt 22:35

3M ago22:35

22:35

In this episode, I was lucky enough to interview Lamees Butt, SVP of Zoovu. Lamees delved into her journey from a humble upbringing in East London to her current role in the tech industry. Growing up in East London instilled in Lamees a hunger for success and a drive to think outside the box. Despite facing challenges, she pursued her passion for e…

1
The First Customer - How to Tackle Tech Complexity to Scale Your Business with Brian Childress 20:53

3M ago20:53

20:53

In this episode, I was lucky enough to interview Brian Childress, Founder and Fractional CTO of Summit Labs. Brian shares his journey from growing up in Virginia to founding Summit Labs, inspired by his grandfather's entrepreneurial spirit as a custom home builder. Despite lacking initial tech interest, Brian discovered his passion for software dev…

1
#58 - Navigating Partnerships w/ Chris May 34:07

3M ago34:07

34:07

In this conversation, Chris May shares his experience of starting his own insurance agency and navigating a partnership. The conversation covers topics such as getting started in the insurance industry, the decision to start a partnership, the importance of clear communication and expectations, and the process of ending a partnership. Chris emphasi…

1
The First Customer - Solving The Most Common Pain Points of ServiceNow Customers with Ron Gidron 23:34

3M ago23:34

23:34

In this episode, I was lucky enough to interview Ron Gidron, the CEO and founder of xtype, a platform engineering solution for ServiceNow customers. Ron shares insights from his background growing up on a farm in Israel to becoming an entrepreneur in the tech industry. Despite his humble beginnings, Ron's journey led him to work with companies like…

1
The First Customer - Aligning Business and Strategies for Superior Performance with Barbara Spitzer 24:05

3M ago24:05

24:05

In this episode, I was lucky enough to interview Barbara Spitzer, CEO and founder of Two Rivers Partners, LLC. Barbara grew up as an army brat and moving frequently, Barbara developed resilience and anxiety, which later shaped her career as a consultant. Despite her anxiety, Barbara adopted a mantra of perseverance and preparation, which helped her…

1
The First Customer - Structuring Your Coaching Empire with LB Trucks Coaching CEO Laura-Beth Trucks 30:46

3M ago30:46

30:46

In this episode., I was lucky enough to interview Laura-Beth Trucks, the CEO of LB Trucks Coaching. Laura-Beth shares her journey from Alabama to Colorado, where she worked in nonprofit leadership development, to eventually founding her coaching business. After completing her master's degree in clinical mental health, she realized her passion for c…

1
#57 - Planning for Ownership Transfers w/ Erik Garcia 40:53

4M ago40:53

40:53

In the third episode of the series, Carey and Lindsay sit down with Erik Garcia from Plan Wisely to talk about the financial challenges and considerations of ownership transfers in independent insurance agencies. Discussing the importance of emotional and financial readiness, setting clear boundaries, and planning for retirement and succession. The…

1
The First Customer - Empowering Entrepreneurs Worldwide with BOSS Startup Science's Gregory Shepard 50:59

4M ago50:59

50:59

In this episode, I was lucky enough to interview Gregory Shepard, CEO and co-founder of BOSS Startup Science. Gregory shares his journey, highlighting his challenges growing up with autism, dyslexia, and other conditions in a tough environment. Despite adversities, he recalls his entrepreneurial spirit emerging early, from selling Rubik's cubes to …

1
The First Customer - How to Be a Digital Thought Leader and Lifestyle Mentor with Dai Manuel 31:05

4M ago31:05

31:05

In this episode, I was lucky enough to interview the fantastic Dai Manuel, Chief Transformation Officer at DaiManuel.com. Dai discussed his upbringing in Ontario with two entrepreneurial parents and how their work ethic influenced him. He recounted his journey from personal training to selling fitness equipment, highlighting the transition to perfo…

1
The First Customer - Attacking the Hard Market Head On with Innovative Risk CEO Caden Braly 20:18

4M ago20:18

20:18

In this episode, I was lucky enough to interview Caden Braly, CEO and Founder of Innovative Risk. Caden discusses his upbringing in Prosper, Texas, surrounded by a community of entrepreneurs, including his father and grandfather, who instilled a strong entrepreneurial spirit in him. Despite initially being hesitant about entering the insurance indu…

1
#56 - Financial Planning for Agency Owners w/ Erik Garcia 35:11

4M ago35:11

35:11

In this episode, Carey and Lindsay sit down with Eric Garcia from Plan Wisely to discuss the financial planning considerations for agency owners. They cover topics such as starting an agency from scratch, being careful who you take cues from, aligning personal and business finances, and creating cash flow and equity. They emphasize the importance o…

1
The First Customer - Boosting Your Sales and Dominating the Local Market with Founder Patric Shannon 18:26

4M ago18:26

18:26

In this episode, I was lucky enough to interview Patric Shannon, Founder of LeadSnap. Patric delves into his origins in a small town in Dayton, Ohio, and his unexpected foray into professional poker and subsequent transition to entrepreneurship. Patric shares about his early career as a tax accountant and his serendipitous discovery of online poker…

1
The First Customer - Shedding Light on the Future of Meeting AI with Fireflies CEO Krish Ramineni 24:06

4M ago24:06

24:06

In this episode, I was lucky enough to interview Krish Ramineni, CEO and Co-founder of Fireflies.ai. Krish dives into his entrepreneurial journey from Silicon Valley to founding one of the most innovative AI platforms. Krish shares how his upbringing in a family of entrepreneurs fueled his passion for technology and startups, leading him from UPenn…

1
The First Customer - Creating a New Paradigm to Transform Marketing with Susan Coelius Keplinger 31:16

4M ago31:16

31:16

In this episode, I was lucky enough to interview Susan Coelius Keplinger, CEO of Force of Nature. Susan shares insights from her journey as a marketing titan and entrepreneur. Growing up in St. Paul, Minnesota, Susan's path led her to chase the internet dream in San Francisco after college. She co-founded Triggit, an ad tech company, with her broth…

1
#55 - Financially Preparing for Ownership w/ Erik Garcia 36:43

4M ago36:43

36:43

In this episode, Carey and Lindsay sit down with Erik Garcia, owner of Garcia Insurance Services and Plan Wisely, to discuss how future owners can set themselves up for success with preparing their personal finances for ownership. Erik emphasizes the need to start with a clear purpose and align financial decisions with personal values. He also disc…

1
The First Customer - The power of social selling and being likeable with Oshri Cohen 19:52

4M ago19:52

19:52

In this episode, I was lucky enough to interview Oshri Cohen, founder of Red Corner. Oshri delves into his entrepreneurial journey and the evolution of his consulting practice as a fractional CTO. Oshri reflects on his upbringing, shaped by early experiences of independence and resilience due to facing racism. From launching his first business at 1…

1
The First Customer - How To Build a Seven-Figure eCommerce Business with CMO Steve Kilberg 24:32

4M ago24:32

24:32

In this episode, I was lucky enough to interview Steve Kilberg, CMO of SKRP Media LLC. Steve dives into his journey as an entrepreneur and his role in helping businesses grow and sell their assets. Steve shares how his upbringing in Detroit, with a father encouraging independence, shaped his entrepreneurial spirit. Despite initially working for oth…

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