Insurance agency owners: How Greg May launched a specialty casualty MGA from scratch with his brother, said no to the opportunity three times, and bound their first policy in under five months.

Want to grow your insurance agency without burning out or selling out? Book an intro call with Elevate Teams: https://calendly.com/elevateteamsllc/introductory-consultation

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In Episode 25 of Elevate the Hustle, Stan Meytin and Dom Piccirillo sit down with Greg May, co-founder of May Specialty, a growing MGA operating in the excess and surplus lines insurance market. Greg spent years building one of the top specialty casualty teams in the country at Allied World before a private equity firm found him and offered him the chance to build his own business. He said no three times. Then he said yes, wrote a business plan with his brother on a deck in Long Beach Island, New Jersey, and launched May Specialty in 2021.

They bound their first policy in under five months. Then they kept going.

Greg also talks about the weight nobody prepares you for when you hire your first employee and realize you are now carrying his family too, why he built May Specialty with one P&L across the entire country from day one, and the moment a stranger in Newark Airport recognized his brand and he knew it was real.

Oh, and he almost became a high school history teacher and football coach. That story is in here too.

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What you'll hear:

• Why Greg said no to the opportunity three times before finally going for it
• How he and his brother launched May Specialty and bound their first policy in under five months
• The weight of hiring your first employee and being responsible for their family
• Why one P&L across the entire country was a non-negotiable from day one
• The stranger in Newark Airport who recognized the brand and what it meant
• Greg's advice for agency owners sitting on the fence about betting on themselves

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Subscribe, drop a comment, and share this with a founder who needs to hear it. 📩 Want to be on Elevate The Hustle or collaborate with us? Apply or connect here: elevatethehustle@elevateteams.io

✅ Connect with us: Instagram: / elevatethehustlepodcast LinkedIn: / elevate-teams Stan's LinkedIn: linkedin.com/in/stanleymeytin Dom's LinkedIn: linkedin.com/in/dominicpiccirillo Greg May: greg.may@mayspecialty.com | mayspecialty.com

About Elevate Teams: We help insurance agency owners scale operations, hire offshore talent, and grow profitably. Book an intro call: https://calendly.com/elevateteamsllc/introductory-consultation

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Real talk, real stories, and occasionally real bad language.

🌐 Website: elevateteams.io
📷 Instagram: @elevateteams
🔗 LinkedIn: Elevate Teams
🎙️ YouTube: @ElevateTheHustlePodcast

In this episode of Elevate the Hustle, Stan Meytin and Dom Piccirillo sit down with Kim Ades, founder of Frame of Mind Coaching and one of the most respected executive coaches in the entrepreneurial world. Kim started selling back massages on Cape Cod at 10 years old, built simulation-based assessments that tested every measurable trait in high performers, and discovered that emotional resilience beats all of them. She has since coached hundreds of business owners and executives across the USA using a journaling-based methodology that gets inside how a leader thinks and changes it from the inside out.

She also shares the story of an emergency appendectomy, a CT scan that found a mass on her kidney, and a Zoom call from a friend in a hospital gown with stage four bladder cancer and six to nine months to live. And what she built from both.

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What you'll hear:

• Why emotional resilience is the single biggest predictor of success for any insurance agency owner or independent agent
  
  
• The journaling method Kim uses to surface the hidden beliefs quietly running your agency without your permission
  
  
• Why most agency owners come to Kim wanting to grow their revenue and leave realizing the work starts with them
  
  
• The two journaling prompts that will show you exactly what is getting in the way of your growth
  
  
• What great leadership actually looks like when everything around you is out of control
  
  
• How to build emotional resilience as a muscle regardless of where you are starting from
  
  

Subscribe, drop a comment, and share this with an agency owner who needs to hear it.

📩 Want to be on Elevate The Hustle or collaborate with us? Apply or connect here: elevatethehustle@elevateteams.io

✅ Connect with us
Instagram: / elevatethehustlepodcast
LinkedIn: / elevate-teams
Website: / https://elevateteams.io/
Stan's LinkedIn: linkedin.com/in/stanleymeytin
Dom's LinkedIn: linkedin.com/in/dominicpiccirillo

Kim Ades
frameofmindcoaching.com
linkedin.com/in/kimades

Real talk, real stories, and occasionally real bad language.

🌐 Website: elevateteams.io
📷 Instagram: @elevateteams
🔗 LinkedIn: Elevate Teams
🎙️ YouTube: @ElevateTheHustlePodcast

In this episode of Elevate the Hustle, Stan Meytin and Dom Piccirillo sit down with Ryan Hanley, 20-year insurance industry veteran, founder of Rogue Risk, board member at Linkora, and one of the most polarizing voices in the independent agent space. Ryan grew up collecting recyclable bottles at 5am to make $40 before school, got fired from every corporate job he ever had, and somehow became the person the industry tried to silence and couldn't.

He built Rogue Risk from scratch, launched it seven days before New York shut down in 2020, and grew it into the fastest growing small commercial agency in the country. He generated 20 to 25 qualified inbound leads a day from YouTube alone and closed them above 80%. Then sold it. On the same afternoon he signed divorce papers and a new apartment lease.

Ryan also gets into why logarithmic growth is within reach for any established agency owner right now using AI, why most agents are using their best people as data entry clerks, and how a woman calling him cold after reading his blog for three months changed the entire direction of his career.

Oh, and Ryan got blackballed from the Big I national conference twice for telling agents the truth about digital marketing. He kept going anyway.

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What you'll hear:
– How Ryan went from cold calling out of the phone book to generating inbound leads on a $100 budget in 2013
– Why independent agents are not behind because of regulation and who is actually responsible for throttling innovation
– The human optimized business model that let CSRs close qualified leads above 80% at Rogue Risk
– How Ryan built and sold his agency on the same day his marriage ended and what he would do differently
– Why AI makes right now the best time in history to have an established independent insurance agency
– How Linkora is solving the data problem that is holding agencies back from actually leveraging AI to grow

Real talk, real stories, and occasionally real bad language.

🌐 Website: elevateteams.io
📷 Instagram: @elevateteams
🔗 LinkedIn: Elevate Teams
🎙️ YouTube: @ElevateTheHustlePodcast