How Lauryn And Michael Bosstick Because Massively Successful Entrepreneurs


Lauryn and Michael Bosstick host The Skinny Confidential HIM & HER podcast, which has over 16 million downloads.

But it’s almost a side hustle, for them, at this point.

They’ve used their community to launch several successful businesses which now generates over $10,000,000 a year.

And it all started with a blog, The Skinny Confidential.

Lauryn said, “I started blogging 13 years ago and I was like, ‘I’m going to start a blog but I’m going to do it 100 percent, every single day, and I’m not even going to think about making money.’ And that’s my advice to anyone getting started in content creation. Don’t start out with the intention of making money.”

Although, it wouldn’t generate revenue for three years, she looked at her blog as a business from the beginning.

She said, “I was like ‘This is what I’m doing. This is my career. And this is going to happen.’”

The blog took off and soon a podcast, with her husband Michael, followed.

They could have just stopped there and lived a comfortable life making millions of dollars off of their podcast.

But they had the drive, and the passion, to keep pushing forward.

Their first business was the podcast network, Dear Media, which they founded in 2018.

It’s a female focused network that hosts over 50 podcasts and has a following of over 60 million across social media.

Michael said, “Dear Media is a multimillion-dollar business. It’s private equity backed. I don’t think people realize that beyond podcasts, Dear Media is an investor in 10 or 11 consumer businesses. We’re in streaming opportunities, live events and merchandising.”

Some of the brands that they’ve invested in, include: Beekeeper’s Naturals, Canopy, Feel Free Botanics, NEZ and more.

Because of their success, they’re pitched new businesses every single day. But what they look for in a startup can’t always be found on a balance sheet.

Lauryn said, “I am someone who goes mainly off of intuition. I have to like the product. And if I can talk about it seamlessly, and it’s something that I’d use for my family, and it’s aesthetically pleasing and their social presence is strong; then I’ll go to Michael and he’ll look under the hood. He’ll look at the numbers, what they’re offering, how much we should invest, etc.”

Michael continued, “We’re also looking for someone who has the ability to grit though all the pain and pressure that it takes to run a business. To be an entrepreneur, to be someone who lays it all on the line, you have to have an innate ability and also to be born with ‘that thing’ that enables you to think like that.”

They have some advice for aspiring entrepreneurs out there.

Lauryn said, “You have to have that belief in yourself. Because if you’re going to ask someone for money, and you don’t believe in yourself, they can feel that energy. And why would I want to invest in someone who doesn’t believe in themselves?”

And they left us with some great advice for creators.

Lauryn said, “People waste so much time consuming other people’s content. I think being really smart about who you’re consuming and how much you’re consuming. Because if you’re consuming other people’s content, it’s taking away from the energy of creating your own content.”

So, put your phone down and try creating something new today.

Who knows where it will lead. Maybe you’ll end up working with the Bossticks one day.

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