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:

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

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

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

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

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

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

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

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)

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

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

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

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

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

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

“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.”

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

“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:

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

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