Relay and Mike Michalowicz Announce New Season of Hit Podcast "Becoming Self Made," Putting Main Street Success in the Spotlight

As a record number of Americans turn to entrepreneurship, Season 2 provides insights and inspiration for building wealth and long-term financial security through small business ownership

NEW YORK, June 17, 2026 /PRNewswire/ -- Relay¹ ("Relay Financial Technologies, Inc."), the small business banking and money management platform, today announced Season 2 of its video podcast "Becoming Self Made." Hosted by American entrepreneur, lecturer, and Wall Street Journal bestselling author Mike Michalowicz, Season 2 puts small business owners behind the mic to talk about the hard-won lessons and personal transformations that come with building businesses that have become household names.

Following a successful first season, which earned 5-star ratings on Apple Podcasts and Spotify and landed in the top 10% of global podcasts, the show moves past the traditional corporate highlight reel. Instead, it offers an honest, unfiltered look at the messy details that traditional success stories tend to gloss over, giving viewers a glimpse at the vulnerable moments behind the big successes of small business.

The show features its signature "Life Line" segment, in which each entrepreneur shares the struggles, setbacks, and incredible comebacks they experienced throughout their lives that shaped the business owner they became, giving the viewer a unique look at how transformation goes hand-in-hand with building something extraordinary.

This season, Michalowicz holds candid conversations with entrepreneurs spanning the finance, food, music, design, retail and wellness industries on how they've built loyal followings and sustainable operations. Guests include:

• Tiffany Aliche, Founder, The Budgetnista. Tiffany is an award-winning financial educator, bestselling author, and founder of The Budgetnista, a financial empowerment platform that has helped millions of women save, manage, and grow their money.
• Andrew Ahn, Founder, Boo's Philly Cheesesteaks. Andrew founded Boo's Philly Cheesesteaks, a legendary restaurant known for its cult following and community first spirit that brings an authentic taste of Philadelphia to Los Angeles
• Tim Milgram, Founder, TMilly Studios. Tim is a viral choreographer, creative director, producer, and founder of TMilly Studios, a globally recognized dance studio and creative community that has shaped the next generation of dancers and performers.
• Jamie Deering, Founder and CEO, Deering Banjos. Jamie leads Deering Banjos, the world's most respected banjo manufacturer, continuing a family legacy of American craftsmanship while helping preserve and grow musical traditions.
• Dr. Brent Ridge, Co-Founder, Beekman 1802. Brent co-founded Beekman 1802, the best-selling lifestyle and skincare company inspired by life in rural Sharon Springs, New York, and built around the idea of kindness, community, and supporting small-town revitalization.
• David Stark, Founder and CEO, David Stark Design. David is an internationally acclaimed event designer and creative entrepreneur whose studio transforms storytelling, hospitality, and live experiences into immersive moments that bring people together.

"There's never been a better time to be an SMB, but survival takes more than just a good idea," said Mike Michalowicz. "This season, we're talking directly to founders and creators about the gritty reality of building a busines—from the cash flow crunches to the failed big bets that nobody likes to admit. Our guests open up and reveal the tough lessons they've never shared before, giving you the raw truth of what it actually takes to win in entrepreneurship today."

The podcast launched amid a macroeconomic shift. According to the U.S. Census Bureau, a record 5.9 million new businesses were formed in the US in 2025—an 8% increase over 2024. Driven by AI disruption, changing labor markets, and a new generation trading traditional college paths for business ownership. This isn't a temporary spike, but a structural rewrite of the American Dream.

For decades, the dominant narrative was that the primary engine of wealth is in Silicon Valley or climbing the corporate ladder—but the tides have turned. Today's founders are building sustainable wealth turning local service businesses, boutique agencies, and independent brands into highly profitable engines. This new generation is proving that the future of economic power belongs to anyone with the grit to build on Main Street.

"There is a hunger right now to celebrate real people who've achieved incredible success from small beginnings and who've stuck by their communities and built from a place of passion," said Bethany Cantor, Director of Brand at Relay and executive producer of the show, "Relay is committed to seeing more small businesses succeed and take a bigger piece of the economic pie. This show is a love letter to small business and an acknowledgment that while we're conditioned to celebrate success, the real lessons and transformations are in the journey to making it big."

Season 2 episode 1 premieres Tuesday, June 23, with new episodes releasing weekly on Tuesdays at 6 a.m. ET.

Frequently Asked Questions

Q: Who hosts 'Becoming Self Made' Season 2?

A: Season 2 of "Becoming Self Made" is hosted by Mike Michalowicz, an American entrepreneur, lecturer, and Wall Street Journal best-selling author.

Q: What topics does 'Becoming Self Made' Season 2 cover?

A: The podcast focuses on hard-won lessons and personal transformations from small business owners who have successfully built lasting brands across diverse industries including finance, food, music, design, retail, and wellness.

Q: Where can I listen to 'Becoming Self Made' Season 2?

A: Season 2, episode 1 premieres on Tuesday, June 23. New episodes will be released weekly on Tuesdays at 6 a.m. ET. You can find the podcast on all major podcast platforms, including Youtube, Apple Podcasts, Spotify, Castbox.

Q: How does Relay connect with the podcast's theme?

A: Relay, the small business banking and money management platform, created the podcast to provide valuable resources and insights to entrepreneurs. It aligns with Relay's mission to support small businesses by offering tools and knowledge for financial success.

Q: What makes this season different from Season 1?

A: Season 2 continues the same focus on unfiltered small business success stories but introduces a fresh lineup of guests, celebrating Main Street icons that include heritage physical brands, localized food favorites, and service businesses.

About Relay:

Relay is digital banking built to give small business owners the tools and know-how to be great with money. By connecting accounts, cards, bills, invoices, capital, and more together in one place, Relay replaces financial guesswork with real visibility, helping owners turn cash flow from a constant source of stress into a signal they can use to run stronger, more resilient businesses.

For more information, please visit www.relayfi.com

¹ Relay is a financial technology company and is not an FDIC-insured bank. Banking services not related to Relay Capital term loans are provided by Thread Bank, Member FDIC.

SOURCE Relay Financial Inc.