In this episode, Aaron Gordon sits down with Todd Thams, an insurance industry veteran who recently transitioned from running a family insurance business to launching ModAdvisor, a tech-focused start-up. Todd discusses his journey, including the challenges and rewards of making such a significant career pivot. He shares insights on the importance of hard work, resilience, and surrounding oneself with the right people. Todd also reflects on how his family's entrepreneurial spirit has influenced his approach to business. Whether you’re interested in the insurance industry, start-up life, or personal development, Todd’s story is both inspiring and instructive. Tune in for valuable lessons on navigating career transitions and maintaining the hustle no matter where you are in your professional journey.

Get To Know Todd Thames

Todd Thams is a seasoned Workers' Compensation expert and the founder of Mod Advisor, bringing over 20 years of insurance brokerage experience, primarily in commercial insurance. Having served as both a producer and agency owner, he established Mod Advisor in 2020 to analyze and report on workers' compensation experience modification data. The software developed by Mod Advisor aids insurance agents in prospecting and retaining clients by providing detailed reports on claim cost impact, validating experience mods, and forecasting future scenarios. Todd’s mission is to enhance transparency in the insurance industry, simplify the workers' compensation experience, and ultimately save businesses money while promoting safer work environments. Outside of his professional pursuits, he enjoys boating, cycling, golfing, reading, and indulging in craft beer, fine wine, great food, and enjoyable times with friends.

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Mod Advisor

3 Episode Key Takeaways Embrace Change and Pivot Wisely: Todd shared his experience of leaving a comfortable position within his family's insurance business to start ModAdvisor. His story emphasizes that it's never too late to find new opportunities and shift gears if you're driven by passion and see a gap in the market.

Surround Yourself with Supportive People: One of the highlights of our conversation was Todd's acknowledgment of the incredible support he received from colleagues, family, and mentors throughout his startup journey. Building a reliable network can make a noticeable difference in your professional path.

Define and Focus Your Hustle: Todd and his wife recently reassessed their life goals to ensure they were heading in the right direction. This strategic planning allowed them to channel their hustle effectively. It's crucial to periodically revisit and redefine your goals to stay aligned with your purpose.

Show Overview:

01:15 Career Evolution and Industry Pivot

03:30 "Challenges of Small-Town Business"

07:39 Joyful Hustling in Insurance Industry

12:32 Father's Sales Setup Insight

15:05 Frustration with Outdated Insurance Tech

19:14 Challenges in Fundraising for ModAdvisor

22:49 Goal Planning for Life Direction

24:38 Busy Lives of Entrepreneurs

In this episode, Aaron Gordon welcomes guests David Garfinkel and Jason Parker to explore the transformative role of AI in professional writing. Initially skeptical, Garfinkel shifted his perspective after witnessing AI's capacity to streamline content creation, significantly reducing the time needed for tasks like LinkedIn posts and podcast scripts. Parker, initially using AI out of necessity to manage a heavy client workload, discovered its potential to enhance his productivity as a "one-man writing team." The discussion highlights AI's role in alleviating workload stress, augmenting human expertise, and enabling new strategic opportunities. Both guests emphasize the importance of precise input and continuous learning to effectively leverage AI, likening it to training a mentee. While AI enhances and scales existing skills, human oversight remains crucial. Aaron Gordon notes the delicate balance between embracing AI proactively and relying on foundational skills. The episode encourages listeners to adapt to technological changes, underscoring the blend of curiosity and necessity that drives AI adoption in professional landscapes. Get To Know David Garfinkel and Jason Parker

David Garfinkel

David Garfinkel is author of bestsellers and Advertising Headlines That Make You Rich, Breakthrough Copywriting, and The Persuasion Story Code. He has been featured in The Wall Street Journal, Forbes.Com, Entrepreneur Magazine, Fast Company and The Los Angeles Times, and is host of the popular Copywriters Podcast. David has worked as a professional copywriter for 30 years and as a copywriting coach for 22 years. His biggest copywriting and coaching wins include writing a two page direct-mail sales letter for Abacus Travel Management that generated $40 million in sales, coaching CEO Mike Straumietis and his team at Advanced Nutrients which resulted in $5 million in additional profits for the company, and writing an online sales letter for Renegade Network Marketer’s mentoring program which generated in excess of $1 million in three days. Before starting in his direct response copywriting business, David was San Francisco Bureau Chief for McGraw-Hill World News. A once-skeptic about AI, David is now a believer. In addition to copy coaching, hosting the Copywriters Podcast, and authoring books that support entrepreneurs in writing copy that converts, he is the co-owner of Novus AI, a company dedicated to helping businesses write AI copy that doesn't "sound like" AI so that they can increase their productivity and profits.

Copywriters Podcast  https://copywriterspodcast.com/

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Jason Parker

Jason Parker has run a successful copywriting business for the last 20 years. With experience serving top clients such as Markus Heitkoetter, Jack Carter, Tom Busby as well as many other financial businesses, he is an expert in marketing strategy and online advertising.

After feeling "stuck" due to increasing client workloads and skyrocketing contractor costs, he began to develop AI tools out of necessity.  

The tools Jason went on to develop are far from the “flat” sounding AI content most people are familiar with.

Through bots and advanced tools, Novus AI creates copy that sounds exactly like a business’ brand voice, and performs as well as copy written by an A-list copywriter (minus the big price tag).  Jason and his staff copywriter used one of Jason’s custom AI bots to create a webinar for a German client, Markus Heitkoetter of Rockwell Trading. The webinar and email campaign, mostly AI-written, generated close to $1 million US (replay sales included), resulting in their first $1.5M sales month.

He is co-owner of Novus AI which offers AI solutions, both done-for-you and done-with you services.

Jason leads a free Facebook group of over 103k+ members called AI Shortcuts. Additionally, he co-leads a paid Mastermind which teaches overtaxed agency owners and entrepreneurs how to streamline their workload with AI, while delivering extraordinary (and profitable) client results. He is the co-host of the State of the Marketing Union Podcast.

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Prompts anyone can use to make their AI copy more conversational

3 Episode Key Takeaways AI Augments Human Expertise: While AI can't replace foundational writing and marketing skills, it significantly amplifies and scales existing capabilities. Think of it as a power tool that allows you to achieve more without compromising quality.


Efficiency & Precision: AI can drastically reduce the time required to create content. The nuanced use of long, detailed prompts enables AI to produce business-specific, error-free, and conversational content. This not only saves valuable time but also enhances productivity.


Adapt or Become Obsolete: Embracing AI proactively can open new opportunities, transforming professionals into more well-rounded or "full-stack" marketers. Staying updated with AI advancements and learning to provide precise instructions can make the difference between thriving and becoming obsolete.


Show Overview:

01:15  AI-written content can disgust and mislead audiences.

05:19  Perception of AI: Revolutionizing, yet controversial tool.

08:58  AI adoption in business necessary for workload management.

10:32  AI agent wrote LinkedIn posts for book promotion.

12:43  Embrace AI to enhance and adapt hustle.

17:22  AI isn't a magic solution; it also requires talent and skill.

19:17  Mentoring AI involves iterative feedback for improvement.

22:22  GPT-5 promises more autonomous writing capabilities.

26:14  AI enhances, doesn't replace, human expertise.

In this episode, Aaron Gordon and guest Peter Bonney reflect on his journey from aspiring physicist to hedge fund manager, emphasizing the importance of exposure to high achievers despite pursuing a non-traditional path. Bonney contrasts his Ivy League education with his brother's success as a high school dropout turned Boeing employee through Navy-acquired skills, underscoring diverse paths to achievement. He stresses self-evaluation and perseverance, sharing the motivational mantra "Fail early, fail often," relevant to Brazilian jiu-jitsu and business. The episode also delves into the impact of remote work on creativity, emphasizing the value of informal office interactions. Bonney discusses the evolution of his career, the importance of seeking environments fostering initiative, and lessons learned from hard work.

Get To Know Peter Bonney

Peter Bonney is the CEO and Founder of Fastbreak, a SaaS platform designed to simplify and accelerate complex engagements between B2B buyers and sellers. Fastbreak helps sales and pre-sales teams leverage their company’s knowledge and collaborate seamlessly with internal subject-matter experts (SMEs) to make complex deals faster and easier.

He was previously the Co-Founder and CEO of Vendorful. Peter's leadership has helped Vendorful become a key player in the B2B tech space, focusing on making complex procurement processes more efficient and transparent.

Fastbreak RFP Vendorful LinkedIn @peterkbonney YouTube

3 Episode Key Takeaways 1. Value of Diverse Career Paths: Recognize that success doesn't have a single route. Peter highlights how his brother found his path through the Navy and Boeing, demonstrating that prestigious colleges are not the only option for achieving greatness.

2. Importance of In-Person Interactions: Emphasize the unique growth and creativity sparked by physical work environments. Peter and Aaron's discussion underscores how spontaneous office interactions contribute to learning and professional development.

3. Embrace Failure for Growth: "Fail early, fail often" is a mantra for learning and improvement. Peter's experiences in both Brazilian jiu-jitsu and entrepreneurship illustrate that embracing failures can pave the way for eventual success.

Show Overview:

01:15 Peter failed to secure a tech job after college.

05:48 Experienced transformative growth with employer's encouragement.

08:32 Entrepreneurial environment during hedge funds' heyday.

09:53 Align with like-minded; support independence and growth.

15:41 Learning from experienced leaders' open discussions.

17:20 Interpersonal relationships evolve best through informal interactions.

22:04 Growing up in a blue-collar, entrepreneurial environment.

24:56 College taught humbling; little applicable knowledge.

28:47 Evolving from trader to software company leader.

30:39 Embrace failure in jiu-jitsu and entrepreneurship.

In this episode, Aaron Gordon welcomes guest Yaakov Langer, who typically serves as a host himself. They delve into Yaakov's upbringing and creative journey, tracing his evolution from creating comics and newsletters to engaging with platforms like Snapchat, WhatsApp, YouTube, and podcasts. Yaakov emphasizes the need for kosher entertainment in the Jewish community and discusses the careful balancing act of content creation that upholds community values. He shares his philosophy of prioritizing impact overviews, recounts challenges faced, and highlights the significance of knowing his audience. Aaron and Yaakov both stress the importance of ethical considerations in hustle culture. The episode concludes with reflections on the essence of meaningful content and the personal mission to inspire and educate.

Get To Know Yaakov Langer

Yaakov Langer is the host of the Inspiration for the Nation Podcast and the founder of the Living Lchaim Podcast Network, which has impressively grown its YouTube subscribers to 1.4 million. With a dynamic presence in media, Yaakov is celebrated for his role as a podcast host and content creator. He covers a wide range of topics, including those often considered taboo, and is actively engaged in shaping the Jewish community's media landscape.

Instagram X/Twitter Living Lchiam Website X - Living Lchaim Youtube Inspiration For The Nation Youtube

3 Episode Key Takeaways 1. Create Meaningful Content: Yaakov Langer champions the idea of filling voids in media with uplifting and educational content, particularly within the Jewish community. By addressing the lack of kosher entertainment, he showcases how content can inspire and reflect community values positively.


2. Balance Values and Success: In discussing his journey and the wisdom from a "Shark Tank" story, Yaakov highlights the importance of prioritizing values over financial gain. The lesson describes how staying true to ethical principles can lead to both personal fulfillment and unexpected success, as evidenced by the farmer who valued fair pricing.


3. Redefining Hustle Culture: Aaron Gordon and Yaakov Langer collaborate to reframe the concept of hustle, encouraging listeners to focus on what's meaningful to them. They suggest defining personal and professional efforts based on intrinsic goals rather than solely on monetary gains or external pressures, promoting a healthier work-life balance.

Show Overview:

01:23 Grateful for freedom, TV watching childhood.

03:41 No need to apologize for entertainment choices.

08:44 Seeking guidance from sages enhances Jewish life.

12:19 Balancing trauma recognition and pursuit of views

12:55 Working to go viral and make impactful content.

16:47 Ben Shapiro is a dream podcast guest.

20:56 Career evolution often involves unplanned natural progression.

28:04 Defining personal hustle and inspiring hustle culture.

In this episode, Aaron Gordon talks with financial sector professional Frank Saraco about the unpredictable nature of career paths and financial decisions. Saraco reflects on his early success in the mortgage industry and the abrupt downturn that forced him to pivot and rebuild his career. He openly discusses regrets, such as not investing in rising opportunities like Bitcoin or restarting his mortgage career in retail sooner. With insights into market dynamics, Saraco also shares his views on the current housing market, interest rates, and broader economic challenges. The conversation delves into maintaining a balanced mindset, valuing integrity over profit, and learning from failures, using motivational stories such as Kobe Bryant's positive mindset after missing a game-winning shot. The episode underscores the importance of resilience and continuous effort in the face of setbacks.

Get To Know Frank Saraco

Frank Saraco serves as the Branch Manager at Cross Country Mortgage and is an Executive Board Member of The Collab Project. With extensive knowledge of the mortgage industry, he provides personalized service and guidance to help clients navigate the changing market and financing options. 

Committed to exceeding client expectations, Frank offers a variety of loan programs and decision-making tools on his website. He is always reachable via phone, text, or email, ensuring expert support is readily available. Trust Frank Saraco as your dedicated partner in achieving homeownership.

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3 Episode Key Takeaways 1. Financial Foresight: Frank Saraco's reflections on his past financial decisions emphasize the value of investing wisely instead of spending impulsively. His hindsight on the missed opportunities like Bitcoin serves as a reminder that foresight and strategic investment are crucial in building lasting wealth and stability.

2. Pivoting Successfully: Frank Saraco's career transition from the mortgage industry to sectors like private equity and insurance highlights the importance of adaptability. His experience underlines that when faced with industry decline, pivoting and starting fresh in a new field can lead to significant growth and new opportunities.

3. Learning from Setbacks: Influenced by Kobe Bryant's mindset, Frank Saraco stresses the importance of viewing failures as learning experiences. Staying positive and resilient can transform setbacks into stepping stones for improvement, reinforcing the significance of perseverance and continuous effort in achieving long-term success.

Show Overview:

01:23  Economic crash taught Frank resilience and planning.

09:52  Mortgage industry was traumatic due to cycles.

11:07  Industries reform, causing adjustment to new norms.

16:15  Modern trend: mortgage-free inheritance decreasing in America.

16:51  Homes become generational assets due to debt.

20:04  Business integrity matters above financial losses.

23:13  Joe Rogan: Failure is good, stay motivated.

In this episode, Aaron Gordon chats with Frank Sentner, a revered mentor in the insurance industry with over 50 years of experience. Known as the "Godfather of Insurance," Frank discusses his shift from fee-for-service consulting to equity-for-service, mentoring InsurTech startups. He emphasizes the importance of receptiveness to mentorship and mutual learning, highlighting successful exits and decision-making strategies for entrepreneurs. Frank shares insights on the enduring role of independent insurance agents, despite technological advancements. He also delves into the dynamics of cofounder partnerships, communication challenges, and the evolving nature of mentorship in a remote work setting. With personal anecdotes and practical advice, Frank illustrates the ongoing relevance of technology and mentorship in the insurance tech space. The episode concludes with a motivational quote from the Dalai Lama, underscoring the theme of proactive happiness.

Get To Know Frank Sentner

Frank Sentner has been providing technology solutions to the insurance industry for nearly 50 years. His consulting practice focuses on improving the business processes of insurers, insurance brokerage firms, and insurance technology solution providers. He has managed significant projects involving the replacement of policy, billing, and claims systems for insurers, as well as providing strategic consulting for large insurance brokerage firms. Recently, he has dedicated several years to mentoring startup InsurTech firms.

In 1976, Frank led the development of the first ACORD forms-based agency policy and claims system while working for Insurnet. He started his consulting firm in 1982 and merged it with two other founders in 1984 to form Creative Information Systems (CISCo). There, he designed and developed Sagitta, the first ACORD AL3-based agency system, which continues to be used by some of the largest insurance brokers in the world.

In 1992, CISCo merged with the Gemini division of Aetna to create CISGEM, which was acquired by Vertafore in 1995. Frank served as Senior Vice President of Technology until 1996. Vertafore was subsequently acquired by Bain Capital Private Equity and Vista Equity Partners from TPG Capital for $2.7 billion in 2016 and was sold to Roper Technologies for $5.35 billion. Sagitta remains their flagship product for national insurance brokers such as Marsh MMA, USI, and BB&T.

In September 1996, Frank started his second consulting practice, Sentwood Consulting. Over the past 26 years, he has consulted for a wide range of organizations, including The Council of Insurance Agents & Brokers, USI Insurance Services, Insurity Inc., and ACORD.

In 2016, Frank collaborated with representatives from the State of Connecticut, the City of Hartford, the University of Connecticut, and several insurers to establish the first InsurTech Accelerator in Connecticut. He has mentored many of its startups, along with those participating in the Nassau Financial Group Re/Imagine InsurTech Incubator. He also serves on the advisory board of InsurTech Hartford. In 2013, Frank shifted his consulting practice from a fee-for-service model to an equity-for-service model. Currently, he is on the board or advisory board for nine InsurTech startups, holding equity stakes in some. One previous startup client has failed, one has successfully exited, and he has retired from the board of another former client company. His only remaining corporate consulting client is ACORD. LinkedIn

3 Episode Key Takeaways 1. Mentorship's Double-Edged Sword: Frank Sentner underscores the pivotal role of receptiveness in mentorship. He emphasizes that while mentors provide critical, honest feedback to foster growth, mentees must be willing to accept constructive criticism. This flexibility is key to avoiding costly mistakes and nurturing professional development, highlighting that mentorship is a mutual growth process.

2. Adapt and Anticipate Change: Drawing from his long-standing career, Frank Sentner speaks on the necessity of anticipating change, especially in tech-driven industries like insurance. His lifelong passion for science fiction enabled him to foresee trends and adapt swiftly. He argues that industries, especially insurance, should embrace technological advancements at a faster pace to stay relevant and competitive.

3. Building Strong Partnerships: According to Frank Sentner, successful business ventures often stem from cofounder partnerships where roles are clearly defined between business and tech responsibilities. He points out the common communication challenges between domains and suggests an intermediary can bridge gaps, ensuring harmony and effective collaboration. His insights stress the importance of clear communication and strategized role division in driving startup success.

Show Overview:

01:23 Frank is considered a major influential figure.

04:00 How can young professionals attract a mentor?

06:34 Father involved in successful insuretech company.

12:36 Three-party collaboration strengthens business-technology alignment.

16:32 Mostly mentor without equity to assess fit.

18:21 Adapting to change without becoming outdated.

22:13 Career evolution is underestimated despite incremental progress.

26:23 Successful timing and technology adoption in business.

In this episode of Keep Hustling, host Aaron Gordon sits down with Dana Ayers, a dynamic professional whose career spans from the White House to military service. Dana shares her journey, discussing her early life influences, her days as a White House intern during 9/11, and how those experiences shaped her drive for public service. She recounts her non-traditional path to joining the military in her 30s and the profound impact of serving in Afghanistan. Dana reflects on her experiences in high-pressure environments like FEMA during Hurricane Katrina and emphasizes the importance of resilience and seizing unexpected opportunities. The episode concludes with Dana's favorite motivational quote by Howard Thurman, encapsulating the essence of her journey: "Don't ask what the world needs, ask what makes you come alive and go do that."

Tune in for an inspiring conversation about hustle, leadership, and the power of embracing challenges.

Get To Know Dana Ayers

Dana Ayers has spent the last couple decades burrowing her way into all sorts of places she had no business being, including herding celebrities in green rooms, working as an armed communicator in Afghanistan, serving as a White House staffer, and conducting media interviews on national television after running all night and changing in a Gold's Gym bathroom.  Her goal is to encourage readers to go after their dreams even if they don’t fit the traditional mold — and even if they’re a bit of a hot mess, like she often is.

Dana considers herself an "ambassador for the unlikelies" which she describes as those who refuse to talk themselves out of unlikely goals. 

Ayers has appeared on Morning Shows in major national markets such as Good Morning America, WGN Chicago, and Great Day D.C., along with dozens of media interviews for print, radio, and podcasts including SiriusXM Radio and Women’s Running magazine.

She holds a master’s degree in Communication from Johns Hopkins University and is the author of the international bestseller Confessions of an Unlikely Runner, and a co-author of Chicken Soup for the Soul: Running for Good. She can typically be found putting coffee before important responsibilities and dreaming up new ridiculous goals to attempt, like starring in her own TV show where she simultaneously competes in a vocal competition while fixing up an old house. 

 DCDana Website

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3 Episode Key Takeaways Embrace a Nonlinear Path: Dana Ayers' career journey demonstrates that success doesn't always follow a straight line. From an unexpected start at the White House to significant experiences in the military, her story shows the value of staying open to diverse opportunities.

Find Life’s Work Through Passion: Dana's experiences highlight that what truly drives success is enthusiasm and dedication. Her quote from Howard Thurman, "Ask what makes you come alive and go do that," reflects the essential need for passion in one's endeavors.

The Strength of Community and Support: Throughout her career, Dana emphasizes the importance of camaraderie, whether through familial support in her upbringing or the bonds formed in the military. These relationships provide the foundation for perseverance and achievement.

Show Overview:

01:12 Excited to explore Dana’s fascinating background map.

03:10 Hustles stem from unnoticed, supportive parental influence.

07:10 Bush administration shaped my adult life significantly.

11:30 Unexpected moments shape our hustle's impact.

13:12 Regretted not serving, eventually inspired by peer.

17:45 Camaraderie requires challenges; builds impactful relationships.

22:07 Fear of boredom drives diverse career pursuits.

23:40 Perseverance proves naysayers wrong; incredible story shared.

In this episode, Aaron Gordon chats with Aryeh Rephun, a young entrepreneur who has carved a niche for himself in the competitive jewelry industry. Aryeh shares his journey from a mischievous childhood in Queens, NY, to navigating law school and transitioning into jewelry sales. Without the benefit of family connections, he emphasizes the critical importance of building trust with vendors, suppliers, and clients through personal attributes like honesty, personality, and hard work. Aryeh and Aaron discuss the unique challenges of the jewelry business, where trust can't be easily validated by clients. Aryeh explains how investing time in relationships and prioritizing client education over quick sales are key to long-term success. The episode delves into Aryeh's belief in spiritual guidance and personal effort driving unexpected successes. Aryeh concludes with a favorite motivational quote, "The dream is free. The hustle is sold separately," and both he and Aaron encourage listeners to remain curious and engaged. The dynamic energy of Manhattan and the critical role of instinct and perseverance in business also feature as highlights.

Get To Know Aryeh Rephun

Aryeh Rephun is a distinguished expert in custom jewelry and the influential founder of Aryeh & Co., a premier bespoke jewelry company based in New York. With years of experience in luxury goods and jewelry, Aryeh has honed his expertise in offering an exquisite selection of precious gems and diamonds. 

Transitioning from standard business practices to establishing his own brand, he has built a reputation for excellence in craftsmanship and design. Aryeh's approach to business is rooted in trust and the development of personal relationships with his clients, ensuring a personalized experience that reflects their unique tastes and preferences. His commitment to quality and customer satisfaction sets Aryeh & Co. apart as a leader in the bespoke jewelry market.

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3 Episode Key Takeaways Building Trust Without Connections: Aryeh Rephun underlines the importance of building authentic trust in his business, especially as he did not have family connections to leverage. By focusing on genuine relationship-building and showcasing his personal attributes like honesty and willingness to invest, Aryeh's journey highlights that trust can be cultivated through consistent efforts and integrity.

Risk and Reward in Business: Both Aryeh Rephun and Aaron Gordon discuss how seasoned professionals continue to take risks despite past setbacks. Aryeh's experience emphasizes the necessity of taking daily risks and having the tenacity to identify genuine opportunities. This lesson underscores the value of diligence, hard work, and an inherent drive to push boundaries in achieving business success.

Value of Referrals: Aryeh Rephun illustrates that referrals are the ultimate endorsement in business, viewed as significant validations from satisfied clients. This episode enlightens listeners on the power of cultivating strong customer relationships, where trust and satisfaction naturally lead to referrals, bolstering business credibility and growth.

Show Overview:

01:25 A young Aryeh was rebellious but likable, resisted conventional classroom rules.

04:28 Trust and relationships ease entry into jewelry industry.

09:27 Taking a pay cut to follow passion.

12:50 Trust builds from investment, education, and authenticity.

14:27 Develop genuine trust without over-promising confidence.

18:44 Industry trust crucial for jewelry business success.

21:17 Unique hustle leads to success and longevity.

25:32 Business involves daily risk and dedication.

In this episode, Aaron Gordon sits down with Matan Slagter, founder of Armadillo, to delve into the intricate journey of building a small business from the ground up. Matan shares his experiences adapting to new roles, emphasizing the importance of flexibility, trust in team members, and the art of delegation. Discover how Matan's diverse career in the insurance industry equipped him with the skills and insights to launch a successful InsurTech startup amidst the challenges of the COVID-19 pandemic. Aaron and Matan explore the highs and lows of entrepreneurship, the value of a solid leadership team, and the wisdom behind striving to make oneself "obsolete" as a leader. Join us as we uncover valuable lessons on resilience, innovation, and maintaining a hustler's spirit in the face of adversity.

Get To Know Matan Slagter Matan Slagter is the Co-Founder and CEO of Armadillo, a platform offering subscription-based home warranties. A former Managing Director at AIG, he has extensive experience in the insurance industry, having started as an actuary and most recently leading market disruption for AIG's personal insurance business. Recognizing a gap in the home warranty market, Slagter launched Armadillo with co-founder Lansdon Robbins, which recently debuted in 20 markets and has partnered with Hornbeam Insurance to support its offerings. Slagter holds a degree from Binghamton University.

LinkedIn Armadillo Website

3 Episode Key Takeaways 1. Flexible Thinking is Crucial: Matan emphasizes the importance of evolving as a leader and being open to new ideas. Flexibility allows founders to delegate responsibilities and build competent leadership teams effectively.

2. Trust in Your Team: Building trust in capable team members is essential. Matan highlights how trusting others and developing a strong leadership team is vital for the growth and sustainability of any business.

3. Innovative Solutions: Armadillo provides homeowners with qualified technicians for home repairs, akin to roadside assistance for homes, showcasing how innovative solutions can address everyday needs and disrupt traditional industries. Show Overview: 01:15  Matan's journey: immigrant hustler building a successful brand. 09:28  Insurance: a smart, stable, and interesting career. 12:00  Led innovations in InsurTech at AIG. 15:54  Taking risks is easier after trying stability. 18:08  Startups grow quickly, requiring rapid adaptation. 20:00  Flexibility and delegation are crucial for founders. 23:22  Armadillo is a smaller, caring, and effective insurance company.

In this episode, Aaron Gordon sits down with Kenneth Williamson, an emerging leader in the insurance industry. Kenneth shares his unique journey from studying business management and working at Chick-fil-A to becoming a foundational player at Portal Insurance in Alabama. Kenneth's hustle is exemplified by his remarkable feat of obtaining his insurance license in just four days. He discusses his evolution within the agency, transitioning from sales to a focus on operations and service. Kenneth opens up about his personal struggles with bipolar disorder and how it has shaped his approach to work and life. He emphasizes the value of self-discovery and mental health, advocating for open discussions about mental illness. Kenneth's story is a compelling testament to resilience, teamwork, and the importance of understanding oneself. Tune in to hear about his experiences, insights, and the motivational quote that drives him forward. This episode is a must-listen for anyone looking to find inspiration in the face of adversity and the power of relentless hustle.

Get To Know Kenneth Williamson Kenneth Williamson is the Director of Operations and an Agent at Portal Insurance, where he focuses on cultivating lasting relationships with partners and clients. He began his journey with the company in its early stages, inspired by founder Bradley's visionary leadership. Kenneth's prior experience at Chick-fil-A equipped him with valuable skills in customer relations and teamwork. He further refined his relationship-building abilities at Experiential Design Group, embracing a foundation of optimism in business. Kenneth is passionate about contributing value to his community while supporting the success of those around him.

LinkedIn Portal Insurance 3 Episode Key Takeaways 1. Embrace Self-Discovery: Understanding your personality and unique traits can significantly impact personal and professional growth. Kenneth's journey through the Enneagram test made him realize his strengths and passions, allowing him to thrive in his role.


2. The Importance of Mental Health Conversations: Kenneth's transparency about his struggle with bipolar disorder highlights the necessity of open discussions regarding mental health. These conversations not only help in personal development but also foster supportive work environments.


3. Seizing Opportunities with Hustle: Kenneth's story of obtaining his insurance license in just a few days demonstrates the power of seizing opportunities with determination and hard work. His relentless pursuit of his goals and quick action exemplify the core theme of hustling.


Show Overview: 01:00 Kenneth, first coworker on the Keep Hulsing podcast.

05:27 Unique Alabama businessman: Bradley Flowers the visionary.

09:08 Balancing strong personality with societal norms.

11:52 Many prioritize money in sales over passion.

14:17 Reflect on achievements before pursuing next goals.

16:48 Personal growth leads to embracing greatness.

21:57 Assessment revealed potential bipolar disorder, seeking control.

23:20 Embracing chaos can lead to personal growth.