In this meaningful and high-energy episode, host Dustin Serviss sits down with longtime friend and StreetText co-founder Stephen Whiting to reflect on 20 years of friendship, entrepreneurship, and perseverance through reinvention. From selling real estate and dreaming of James Bond-level freedom, to co-founding a tech company that now powers lead generation for thousands of agents, Stephen shares his unconventional path and the lessons learned along the way.

They dive into:

• Why Stephen never wanted a job—and how that shaped his early career moves
• The origin story of StreetText and its pivots from SMS sign toppers to Facebook ad automation
• How a near business breakdown at a Facebook conference led to a game-changing fix from an anonymous insider
• The evolution of paid ads and how StreetText survived the iOS14 privacy blow
• Lessons on startup failure, mastermind friendships, and how to validate ideas without giving up too soon
• The role of mentorship, intention, and even divine timing in building a meaningful business
• Why sharing your story, even when it feels scary, can create ripple effects you’ll never see

This episode is packed with raw honesty, behind-the-scenes wisdom, and heartfelt stories from the trenches of entrepreneurship. If you’ve ever struggled with change, questioned your vision, or wondered whether your story matters—this one’s for you.

Connect with Stephen Whiting:

LinkedIn: Stephen Whiting

Website: streettext.com/

01:02 Early Business Ventures and Real Estate

05:27 The Birth of Street Text

08:46 Challenges and Lessons Learned

14:52 Navigating Changes in Digital Marketing

20:49 The Impact of Apple's Privacy Changes on Facebook Ads

22:34 Apple vs. Facebook: The Privacy Battle

24:22 The Importance of Networking and Mentorship

26:17 Overcoming Business Challenges with Faith and Determination

32:22 The Power of Visualization and Positive Thinking

36:35 The Value of Sharing Your Story