Founder2Founder with Aaron Spivak
Entrepreneurship isn’t just a career—it’s a relentless, all-consuming way of life.
Welcome to Founder2Founder a raw and unfiltered podcast where host Aaron Spivak pulls back the curtain on what it really takes to build something from the ground up. No sugarcoating, no overnight success stories—just deep, honest conversations with some of the most driven, underrated, and game-changing founders of our time. From brutal setbacks to game-changing mindset shifts, Aaron goes beyond the polished success stories to uncover the unglamorous, deeply personal side of building a business.
As a seasoned entrepreneur himself, Aaron goes beneath the surface and gets into the nitty-gritty of what it truly takes to succeed. He’ll dive into the habits, behaviors, and routines that set elite founders apart, the tactics and strategies that are working today, and the mindset shifts required to push through the hardest moments. Through raw personal stories, late-night struggles, and breakthrough moments, guests open up about what it really means to grow, not just as a founder, but as a person.
Each week, Aaron sits down with visionary entrepreneurs from high-growth startup founders to seasoned CEOs, for real, unfiltered conversations about the highs, lows, and everything in between. Whether you're scaling a company, launching your first venture, or just looking for inspiration, this podcast will give you the insights, motivation, and real-world advice you won’t get just anywhere. If you're ready to strip away the illusion and get real about what it means to build, sacrifice, and thrive, this is the podcast for you. Join us every Wednesday!
Founder2Founder with Aaron Spivak
Canadian Founder Exodus: Mena Maimone on Leaving Canada, Building in the U.S. and Visa Strategies
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In this episode of Founder2Founder, Aaron Spivak sits down with immigration attorney and founder Mena Maimone for a direct conversation about why so many Canadian entrepreneurs are exploring a move to the United States. Originally from Canada, Mena moved to South Florida nearly a decade ago, earned her J.D. from Nova Southeastern University, and built Maimone Legal with her mother into a fast-growing firm helping clients navigate the move to the U.S.
Together, Aaron and Mena unpack the fears, misconceptions, and real opportunities behind relocating as a founder. From visa pathways and taxes to safety, lifestyle, and long-term freedom, this episode offers a clear look at why more entrepreneurs are making the move and what it actually takes to do it well.
Chapters:
01:30 – Why Aaron Believes Canada’s Builders Are Leaving
01:32 – Mena Explains What She’s Seeing With Canadian Business Owners
03:15 – The Main Reasons Canadians Are Looking to Leave
04:41 – What a Government-Heavy Economy Means for Entrepreneurs
05:11 – The Importance of Environment, Energy, and the “Miami Effect”
06:09 – The Biggest Hurdles Canadians Think They Face
06:12 – Why Mena Says the Process Is Easier Than Most People Think
07:47 – Advice for Founders Who Want to Leave but Feel Stuck
09:04 – The Fear-Based Mindset That Keeps People From Making the Move
10:23 – The Most Common Objections Mena Hears
11:09 – Debunking the Healthcare Cost Myth
13:42 – Why the Quality of Life in Florida Feels So Different
16:47 – Why Mena Believes Canada Is Trying to Slow the Exodus
18:02 – Choosing Your Environment and What That Says About Your Future
19:31 – Aaron Shares the Home Invasion That Changed Everything
25:07 – What Founders Need to Know About the So-Called Exit Tax
28:12 – What It Typically Costs To Make the Move Properly
29:05 – How Mena’s Business Has Doubled and What Markets She’s Watching
30:00 – Why Asset Protection Matters More in the U.S.
31:10 – Tax Advantages Business Owners Often Overlook
34:41 – Building a Business With Family and Creating a Legacy
38:40 – Why the E2 Visa Is One of the Most Popular Paths
39:52 – How Long E1 and E2 Visas Last and What Renewal Looks Like
42:38 – Green Card Options for Founders Who Want a Long-Term Path
Guest Links:
- Instagram: @maimone_legal
- YouTube
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