Steven Perry’s story is one of grit, reinvention, and making the leap—from commercial fishing in Alaska at 14, to making nearly $1M/year running Fortune 100 teams, then burning the boats to launch his own recruiting firm. As founder of The Well Recruiting Solutions, he now builds revenue-generating teams for advisory firms, aiming to empower 1,000+ clients by 2030.

On this episode we talk about:

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  Early hustle: commercial fishing in Alaska, learning at 14 the difference between working for a check and owning the business

  
  


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  His first true entrepreneurial venture—sealing driveways, scaling a six-figure business by the end of college, and the lesson he learned when he simply shut it down instead of selling it

  
  


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  Why Steven ultimately turned down a prestigious ROTC scholarship and a Navy career path to pursue entrepreneurship and finance

  
  


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  His entry into financial services, starting as an intern at New York Life, becoming a top-producing advisor, and why being surrounded by high performers forced him to level up

  
  


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  Lessons from sales and financial advising—mastering rejection, discipline, and the numbers game ("Whoever’s willing to be told 'no' the most wins fastest")

  
  


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  How being in the right environment and seeing other people succeed reframed what's possible, pushing him to greater heights

  
  


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  Reaching financial milestones by 30—making $500K/yr, giving away and saving large percentages, but discovering money alone doesn't bring fulfillment or lasting happiness

  
  


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  The personal finance strategy that enabled freedom: maximizing cash value life insurance and variable universal life for tax-free, flexible, and compound growth (plus why he prefers guaranteed accounts over variable for business owners)

  
  


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  Navigating the transition out of a lucrative corporate job: searching for purpose, listening to intuition, and eventually being "pushed" into launching his own firm after a job opportunity disappeared

  
  


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  How The Well Recruiting Solutions emerged from listening, networking, and recognizing a deep need for white-glove recruiting in wealth management; now scaled to nearly 30 employees with a future goal of $1B in revenue

  
  


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  The difference between grinding for someone else and building for yourself—now hiring for his strengths and delegating everything else for maximum impact and fulfillment

  
  

Top 3 Takeaways

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   Ownership > High Salary: Building long-term wealth and fulfillment comes from owning and growing businesses, not just earning a high paycheck.

   
   


2. 
   

   Skill Stacks Compound: Every job, network, and hard moment (from fishing boats to insurance sales) built the resilience and expertise needed for entrepreneurial success.

   
   


3. 
   

   Freedom is Designed: Smart moves—like flexible, tax-efficient investments—enable you to take risks, start over, and say yes to your true calling without fear.

   
   

Notable Quotes

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  “I looked up and had a great income, but I didn’t own anything. The day I left was the day there was no more equity, no more income.”

  
  


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  “Whoever’s willing to be embarrassed, to be told no, the most—wins the fastest.”

  
  


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  “If you operate in your gifting all day, you’ll be more profitable and productive. Now, if I don’t want to do something, I can hire someone who does it better and faster.”

  
  

Connect with Steven Perry:

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  Recruiting for advisory/financial services: The Well Recruiting Solutions https://thewell.solutions/

  
  

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