115: Crazy Business Stories: Heather’s Webinar Woes
Running a business is never a smooth ride. It is messy, unpredictable, and sometimes downright hilarious.
In this episode, Heather shares some of her craziest webinar stories (think paper shuffling, awkward silences, and epic tech fails). She talks about the early days of running live webinars, the time she completely lost internet connection during a big sales pitch, and what it is like trying to juggle business when family emergencies pop up.
Mixed in with the stories, Heather gives tips for hosting webinars and shows how her background in teaching turned out to be a huge advantage in entrepreneurship. More than anything, this episode is a reminder that you are not alone in the business chaos.
Mistakes and messy moments are not just normal, they are part of the journey, and often lead to the best lessons – and the funniest stories!
Key Takeaways:
- (02:55) Overcoming the fear of being live on camera
- (05:50) Heather’s early webinar struggles
- (13:30) Tech fails in real time; losing internet during a webinar
- (19:45) Balancing business and family; when emergencies happen mid-webinar
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Embracing the Chaos: Crazy Webinar Stories and What I Learned About Building a Teacher Biz
Running an online teacher business is never as smooth as it seems. In this episode of the Teacher Biz Podcast, Heather shares her wildest webinar mishaps and what she’s learned from rolling with the punches.
If you’ve ever doubted yourself during a live event or launch, this one’s for you.
Webinar Nerves: Why Going Live Feels So Scary
Webinars are a cornerstone of selling and teaching online, but the idea of going live—teaching and selling in real-time to a group of strangers—is enough to send most new business owners running.
Heather freely admits that she avoided webinars for years, making excuses about her schedule and her home setup. But under the surface, it was really about fear: What if I mess up? What if nobody buys? What if they’re making fun of me behind their screens?
Her honesty here is reassuring: “I was shaking in my boots.” And yet, that fear is just part of the growth process.
Learning to get comfortable on camera, knowing how to pitch, and finding your own “voice” all come from repeated, imperfect practice—not from waiting until you’re perfect.
Lessons from Webinar Fails (And Why They Matter)
1. Practice Makes Progress (Even if You Stumble at First)
In her early days, Heather hired a team member, Alexis, just to sit in on webinars and help manage the chat. The first run-through was rough: Heather read everything off printed paper notes, making distracting noises on the microphone, losing her place, and feeling flustered. But with time, she shifted to digital notes, got comfortable speaking for longer stretches, and learned to build in moments for water and recovery.
The takeaway? Your first attempt will feel awkward, and that’s okay. Don’t let imperfection hold you back—confidence grows from doing, not preparing.
2. Tech Glitches Happen (Even at the Worst Time)
Heather recalls the heart-stopping moment when her internet died—right at the critical point when she began pitching her course at the end of a major webinar.
With a significant ad budget riding on this event, the stakes were incredibly high, and losing connection could have been disastrous. But thanks to Alexis holding down the chat and keeping attendees calm, Heather was able to bounce back, pick up where she left off, and still make sales.
No matter how well you prepare, tech can fail. What matters most is your ability to stay calm, reorient, and keep going. As Heather’s story shows, audiences are generally kinder and more understanding than we fear.
3. Sometimes, Nobody Buys—And That’s Part of the Game
Not every webinar is a home run.
Heather shares a humbling story where, after pouring her heart and energy into a session, not a single participant bought her offer. In another instance, the only purchaser requested an immediate refund.
These moments sting but are a rite of passage for every business owner. They’re reminders to separate your self-worth from individual outcomes and keep going.
Family Interruptions & Real-Life Chaos
Webinars aren’t the only thing that can go sideways. During one key live VIP call, Heather’s son’s school called—requiring her husband to step in for a family emergency while she continued teaching.
Juggling business and family obligations is tough, but these stories normalize the juggle we all face.
Heather’s stories are more than entertaining—they’re vital reminders that no one escapes mistakes or awkwardness in the journey to building a teacher business. Rolling with the punches, adapting, and maintaining your sense of humor are must-have entrepreneurial skills.