Season Two of ‘The First Million Is Always The Hardest’ Podcast Set to Air in Partnership with WGN

Veteran business owners and trailblazing developers among highlights in the new season

The success of Season One affirmed that The First Million is Always the Hardest speaks to a powerful truth about entrepreneurship and perseverance.”

— Bo Kemp, Host and CEO of the Southland Development Authority

TINLEY PARK, IL, UNITED STATES, November 10, 2025 /EINPresswire.com/ -- Host Bo Kemp and the Southland Development Authority (SDA) have announced exciting plans for the second season of “The First Million Is Always The Hardest”, one of the region’s most insightful and fastest-growing podcasts exploring entrepreneurship, business, and real estate development.

With ten engaging episodes already under its belt and a new partnership with WGN Radio,

“The First Million Is Always The Hardest” is poised to expand its impact and reach, continuing its mission of bringing hands-on, practical lessons of entrepreneurship and wealth building to audiences across Chicagoland and beyond.

“The success of Season One affirmed that The First Million is Always the Hardest speaks to a powerful truth about entrepreneurship and perseverance. We’re honored to partner with WGN for Season Two and appreciate Dane Neal and his team for recognizing the impact and potential of this platform,” said Bo Kemp, CEO of the Southland Development Authority and host of The First Million Is Always The Hardest.

Season Two raises the bar with bigger ideas, bolder conversations, and even more inspiring voices contributing their perspectives. Some highlights of the upcoming season include explorations of business growth in the face of uncertain market conditions, stories of successful entrepreneurship across different decades, and the remarkable journeys of military veterans who have transformed their service experiences into successful business ventures.

A focus in the first episode of Season Two—veterans will share how they translate the discipline, teamwork, and resilience garnered while in military service into thriving opportunities in the private market. The conversation will focus on the suitability of characteristics commonly found among military veterans for leading businesses and achieving success in entrepreneurial pursuits. Listeners will gain real-world insights on leadership and adaptability directly from those who have lived it. From trailblazing developers to changemakers across the Southland and beyond, listeners will gain a deeper understanding of how to leverage innovation and integrity to build businesses that make a lasting impact.

“Season One connected with listeners because it showcased real people, real struggles, and real success,” said Dane Neal, host and producer at WGN Radio. “The show has tremendous potential to grow its audience while continuing to inspire and uplift the entrepreneurial spirit that drives our region forward. We’re thrilled to help bring Season Two to life.”

Building on the success of its debut season, the podcast will continue to spotlight the untold stories of nationally acclaimed business leaders, innovators, and investors who have navigated the highs and lows of building their first million—offering tangible lessons that listeners can apply to their own journeys toward success.

Don’t miss a single moment of the valuable conversations in Season Two. Subscribe now on Spotify, Apple Podcasts and YouTube, and follow The First Million Is Always The Hardest on Facebook and Instagram (@thefirstmillionpodcast) to join a growing community of people building wealth, purpose, and legacy every day.