Episode #443

How to Master the Evolution of Your Speaking Business

With Bobby Umar

Bobby Umar is a speaker who does it all. He writes books. He runs coaching programs. He’s amassed hundreds of thousands of followers in his social media communities. He’s done multiple TEDx talks. And most importantly, he’s a self-described doting dad. If you’re wondering how he manages to juggle so many balls alongside his speaking engagements, so are we–so he joined our founder Grant Baldwin for Episode 443 of the TSL podcast to discuss his speaking journey.

Many aspiring speakers want to be like Bobby. All kinds of people in all sorts of industries look to him as a branding and networking expert. But he didn’t start out that way! Over time, he has both expanded and refined his speaking platform so he only speaks on topics he is best at to audiences who are the perfect fit. On the show, he shares how he started with a well-defined niche that allowed him to become a thought leader with a simple, compelling message: discover your personal brand (DYPB).

One part of Bobby’s platform that we don’t often talk about on the TSL podcast is TEDx talks. While not all TEDx talks are created equal, Bobby and Grant walk through how you can decide if this is a useful tool for your speaking business and how to leverage TEDx appearances as part of your marketing plan. This episode is packed full of incredibly important lessons on scaling your speaking business, and Bobby’s charisma shines through every word. To top it off, he offers some wise words on how to prioritize your family while making travel plans. You’ll also learn all about:

  • Realistic timelines for pivoting from your 9-5 to speaking
  • Signals and feedback to listen for when you’re ready to diversify your business
  • The importance of uniting all aspects of your business under a cohesive umbrella
  • How to find an ideal client when you speak on a widely applicable topic
  • What to do when traveling for gigs isn’t worth the time away from family anymore
  • How keynotes are evolving in the virtual space
  • …and so much more!

Want to know exactly how to find and book more paid speaking gigs?

Download our 18-page guide to the 6 proven steps you can use to book more paid speaking gigs in 2026!

About Bobby Umar

Bobby Umar is an inspirational speaker, coach, and one of the most prolific, heart-based leaders in North America. Inc Magazine named him one of the Top 100 Leadership Speakers, alongside such noteworthy giants as Richard Branson, Brene Brown, John Maxwell and Robin Sharma. Bobby is a 5x TEDx speaker, and one of the top influencers in the world, with over 650,000 social media followers. He has been named the 2nd best business coach to follow on Twitter and the 5th best leadership influencer according to Kred. Bobby is an international author of three books, including a #1 best seller, and is a Huffington Post contributor. He hosts a weekly tweetchat called “The Power of Connection” that has reached over 65 million impressions weekly. To date, his social media influence has garnered over 2 billion impressions. Bobby was also named a “2015 Speaker to Watch” and most recently, he was named a Top 7 Networking Guru to follow.

A social media advocate, who champions authentic connection and heart-based leadership, Bobby has appeared on dozens of podcasts, TV & radio shows. With a background in brand marketing (Kraft & Unilever), engineering (Bombardier) and the performing arts (Second City), Bobby has led Raeallan for over a decade and is now a recognized thought leader in Networking, Social Media and Personal Branding. He founded the DYPB – Discover Your Personal Brand conference, the largest event in North America dedicated solely to personal branding, featuring 60 experts and over 300 delegates. Most recently he has become a Social Audio advocate running a 35k+ member community on Clubhouse, Twitter Spaces and LinkedIn Audio. 500,000+ people from across the world have experienced Bobby’s high-energy keynotes, interactive teambuilding activities, and engaging workshops.

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