The Lifestyle Investor - Investing, Passive Income, Wealth

270: A Fresh Perspective for Vetting New Business Deals with Pat Flynn

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Dec 25, 2025

Pat Flynn, an online entrepreneur and creator of Smart Passive Income, shares his journey from being laid off to building thriving passive-income businesses. He introduces his Airport Test framework for evaluating business ideas and discusses the high ROI of advisory shares. Pat emphasizes prioritizing family time over work, fostering community collaboration, and utilizing market maps to validate demand. He also highlights the importance of mastermind groups for accountability and learning, making the case for smart, intentional living.

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ANECDOTE

Early Advisory Payoff

Pat's first advisory role came from Leadpages after they noticed his affiliate performance.
He traded a little time for equity and learned advisory can be semi-passive and lucrative.

ANECDOTE

Advising Platforms Led To Big Wins

Pat advised Teachable and later Circle, which led to major exits and larger payoffs.
Those wins inspired him and Matt to form Super Advisors to co-advise startups.

ADVICE

Set Advisory Boundaries

Avoid advisory roles that demand recurring time; set rules before saying yes.
Structure agreements to focus on introductions and strategic help rather than hands-on work.

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For any entrepreneur, the most valuable currency to buy back is time. Yet many remain trapped, losing time with family and struggling to break free from the business.

But today's guest has become the embodiment of building freedom through creativity, community, and leveraging advisory opportunities.

Pat Flynn is the creator of Smart Passive Income, bestselling author of Will It Fly? and Superfans, advisor to top tech companies such as Teachable, Circle, SquadCast, and Riverside, and one of the most respected voices in online business.

Since being laid off as an architect in 2008, he’s built multiple 7-figure businesses, generating millions of podcast downloads, and launching a wildly successful Pokémon YouTube channel with almost 2 million subscribers.

In this episode, Pat shares how he identifies winning opportunities, his Airport Test framework for evaluating business ideas, how advisory shares became one of his highest-ROI wealth builders, and how he’s intentionally designed his life so that work supports family—not the other way around.

In this episode, you’ll learn:

1.) How Pat turned a layoff into a launchpad for building multiple passive income businesses.

2.) A simple framework to evaluate business ideas before investing time or money.

3.) Why advisory shares became one of his highest-leverage income streams—and the criteria he uses to decide which companies to work with.

Show Notes: LifestyleInvestor.com/270

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