How to Start a Successful Podcast with Jason Lederman
Professional advice and insights from the Winter Park Chamber’s Chief Marketing Officer.
March 9, 2026
Normally found behind the scenes as the producer of the B Student podcast, Winter Park Chamber CMO Jason Lederman steps into the guest seat this week to share his playbook for digital growth with host Betsy Gardner. Drawing on a career of data-driven strategy - from producing his first podcast at VH1 to serving as the first-ever Social Media Editor at Popular Science - Jason reveals why the future of the medium belongs to those who prioritize community over vanity metrics. Whether you're a leader looking to build brand presence or an aspiring host seeking technical tips, this episode offers a masterclass in navigating the 2026 digital landscape.
1. How Social Media Algorithms Rank Podcasts in 2026.
The age of "like and subscribe" is over - it's now the time to "comment and share." The most successful podcasts are the ones that best connect with their audiences. Meaningful engagement, like comments and shares, play a larger role now in how social media algorithms determine what content to send into users' news feeds than likes and follows or subscribing. Watch as Jason explains why your "Share" count is the new gold standard:
2. Podcast Hosting Tip: Master the Art of the Follow-Up Question
According to Jason, the key to successful interviews are follow-up questions and not being afraid to dive deep and letting a guest fully flesh out an idea. The best questions are often the ones you haven't prepared, so don't get too caught up in thinking about what to ask next and miss something! This key skill is hard to develop, but if you want to host a chat show, it is key to developing your podcast hosting skills. See Jason's top hosting tips in the clip below:
3. Find Your Niche in a Saturated Podcast Market
There may be too many podcasts, but there is always room for more. If you have an idea for a show or a format that you're not seeing out in the world, make it! The exciting thing about creating an online show is there is room to experiment and make mistakes. Let your audience and data inform your strategy - sometimes the thing that you enjoy isn't what the audience likes and learning not to be too precious will help you to grow as a podcast producer. Jason shares why your unique perspective is exactly what the market is missing:
4. Why Audience Connection is the Core Tenet of Podcasting
Just as the Winter Park Chamber fosters local belonging, successful podcasters understand that connecting with audiences is the heart of the medium. While traditional media formats are not as accessible, podcasting democratizes the industry, giving anyone the tools to reach their specific community directly. This accessibility allows hosts to build deep, personal bonds with listeners whenever and wherever they are. Watch as Jason explains why meaningful connection is the ultimate success metric for any show:
5. The Two Pillars of Podcast Success: Host + Content
It seems obvious, but the two most importan parts of a podcast are the content and the host. There are podcasts on nearly every topic imaginable, so the determining factor in what audiences seek out is likely the host. By developing your skills to carry a show - no matter the format - you can better connect with your audience and draw in new listeners. Watch Jason break down the two essential pillars of every successful show:
Ready to start your podcast journey?
Don't stop at the highlights. Watch the full episode with Jason Lederman on YouTube to see how the Winter Park Chamber is leading the digital conversation, or subscribe to the B Student podcast on Apple Podcasts, Spotify, or wherever you get podcasts.