The Pick Now Podcast with Jeff Munn

When Everything Falls Apart, Build Something Better with Shashank Shekhar | #27

What happens when you lose your job in a new country with no money, no network, and no backup plan? On this episode of The Pick Now Podcast, Jeff Munn sits down with entrepreneur and author Shashank Shekhar to unpack the remarkable journey from immigrant startup employee to award-winning FinTech founder. After his company collapsed during the 2008 mortgage crisis, Shashank turned uncertainty into opportunity by building a mortgage business centered around education, trust, and technology. What started as late-night blog posts eventually became Instamortgage, one of the fastest-growing mortgage companies in America. Along the way, he taught himself AI, built one of the first AI-powered digital humans in the mortgage industry, and even outpaced Zoom on Deloitte's FastTech rankings during the pandemic. In this conversation, you'll hear: * How resilience beats talent without persistence * Why education became his ultimate business strategy * What founders can learn about AI right now * How to think long-term when building a company * Why limiting beliefs stop more dreams than lack of skill If you've ever wondered whether your big idea is worth pursuing, this episode might be the push you need to start.

From Rock Bottom to $400M Exit with Mike Fata | #26

He went from 320 pounds and rock bottom to building and selling a $400 million company. In this episode, Mike Fata shares how a personal health crisis led him to discover hemp, build Manitoba Harvest from scratch, and navigate two decades of uncertainty, setbacks, and breakthrough growth. From dropping out of high school to becoming a $100M+ CEO, Mike breaks down the mindset shifts that fueled his success and the identity changes required to sustain it. You'll also hear what happened after the exit, including the unexpected personal challenges that forced him to rebuild his life from the ground up and redefine success on his own terms. Key takeaways: * Why "just one more day" is the most powerful entrepreneurial mindset * The difference between being your best self vs trying to be better * How discipline, not motivation, drives long-term success If you've ever felt stuck, overwhelmed, or on the edge of quitting, this conversation will challenge how you think about growth, resilience, and what it really takes to win.

Get Your Financial House in Order with Elke Rubach | #25

What if one hard conversation today could save your family years of chaos tomorrow? In this powerful episode of The Pick Now Podcast, Jeff Munn sits down with founder Elke Rubach to unpack how childhood loss, legal training, entrepreneurship, and personal reinvention shaped her mission to normalize money conversations. From wills and wealth planning to identity, trust, burnout, and family values, Elke reveals why financial planning is about far more than money. It is about protecting the people you love most. In this episode: * Why avoiding money conversations can create generational chaos * How founders and families can build real security through intentional planning * The hidden link between values, trust, burnout, and long-term wealth Your legacy will exist whether you plan for it or not. This episode will inspire you to take control before life does it for you.

One Yes Changes Everything | #24

What if you're just one yes away from changing your entire life? In this episode, Jeff Munn sits down with serial entrepreneur Bryan Lord to unpack the messy, unfiltered reality of building something from nothing. From feeling out of place in college to raising capital off a 14-page deck, Bryan shares how persistence, irrational belief, and a willingness to hear "no" over and over again shaped his journey. They dive into the truth about entrepreneurship that no one talks about—the politics, getting fired from your own company, and why success doesn't always feel the way you think it will. Bryan also reveals why chasing the destination can leave you empty, and what actually matters in the long run. Key takeaways: * Why being a generalist can be your greatest advantage * The power of hearing "no" and still moving forward * Why you're often better off raising capital with just an idea * The hidden downside of "making it" If you've ever felt like you don't fit the mold, this conversation will challenge how you think about success—and what it really takes to build something meaningful.

AI Is Forcing Us To Be Human | #23

What if the rise of AI isn't about replacing us… but revealing who we really are? In this episode, Yen Anderson shares her journey from defense tech to becoming one of the earliest voices inside Microsoft advocating for AI adoption. From experimenting with ChatGPT on day one to influencing thousands globally, Yen explains why AI isn't just a tool. It's a turning point for human identity. Together with host Jeff Munn, they explore what happens when machines take over repetitive work and why the future belongs to those who embrace creativity, psychology, and human connection. Key takeaways: * Why AI will replace tasks, not human potential * The hidden danger of outsourcing your thinking * How to rediscover your identity in an AI-driven world If you've ever questioned your career, your purpose, or your place in a rapidly changing world, this conversation will challenge you to rethink everything.