How to Take Calculated Risks (plus, how I sell sponsorships)

published26 days ago
2 min read

Hey Reader,

Imagine making $70,000…from your bedroom…in one night.

That’s exactly what Matt “Dappz” McGuckin did with his online trading cards shop. He got his start “breaking” – that is, buying and opening boxes of cards live online, and selling the contents…all on TikTok.

Sound risky? It is! But today, Dappz Sports is the top Live Shopping Company on TikTok in the U.S., making over $20 Million in gross the risks have paid off.

Now maybe it seems like too far-fetched to say you’ll make $70K in one night, but it’s not too far-fetched to say that making calculated risks will elevate your business.

It’s a proven strategy and Dappz, and today, he’s going to tell you how you can do it too.

Top Takeaways

  • Don’t try to think about how you’ll go viral. Instead, be consistent and try different things. Experimenting can be low-stakes risk-taking.
  • One of the biggest risks that pay off is hiring someone. They will take SO much off your plate. It sounds scary, but it’s a must for any business owner.
  • Research is SO important with it comes to mitigating risk – remember, this is about calculated risks, not being a cowboy, and doing crazy stuff to see if it pays off.


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Behind the Scenes: How I'm Selling Sponsorships

A couple of weeks ago, I promised I’d share the changes I made to selling sponsorship packages.

See, last year around this time, I was in a bit of a panic. Q4 (Oct-Dec) is usually my biggest quarter for sponsorship and there were crickets. Like, $20K usually, $0 that quarter.

People were throwing around the r-word (recession), so ad budgets had dried up or moved to some other type of content, like newsletters.

At the time, I was selling sponsorships in terms of seasons – and while I did bundle other content, it was an afterthought.

So this year, I decided to try something different.

First, seasons is an unclear term. It means something different to each person and podcast. I opted for selling bundles of weeks. Instead of “half a season” you’d get 12 weeks.

I also added more deliverables in sponsorships – like automatic inclusion in my newsletter, a monthly dedicated section like the one above, and a YouTube video.

This serves two purposes: it allows the sponsor to reach multiple channels, adding more value. But it also gives me a better starting point for negotiation.

If they don’t want the video or the newsletter, I can always remove those and adjust the price, or similarly, place the focus somewhere else (2 videos, but fewer episode spots) and adjust the price.

As you go into 2024, think about the best places you can add value for sponsors – remember, it’s not always about the downloads. It’s also about the perceived value of what you’re offering. And for some brands, an honest video, or honestly talking about their product on your podcast and in your newsletter, is very, very valuable.

Until next time,

Joe Casabona
The Podcast Systems Guy

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