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This week on , I sat down with Bryan Reisberg, who you may know as ‘s better half. Together, they’re one of the most successful dog–influencer duos on the planet. Bryan and Maxine have grown an audience of roughly 7 million followers and turned a simple subway problem into a booming pet brand called , home of the internet’s favorite dog backpack and fast‑growing pet wellness products. In our conversation, Bryan explained how love for his dog, obsessive persistence, and clever partnerships turned his idea into a real company. 

And we’ve broken his best insights down to help you bark up your own personal success in three, two, one!

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Three Key Insights

1. Start With a Problem You Can’t Ignore

Little Chonk didn’t start as a business plan; it started because Bryan was sick of hauling Maxine around in what he calls “a piece of shit” dog backpack that was unsafe and uncomfortable. New York’s MTA had ruled that dogs had to be in carriers, so he tried every bag on the market, hated all of them, and realized “literally thousands of people… wanted something better.” He and his co-founder spent two years designing a backpack despite having “no product design background” and launched on Maxine’s sixth birthday; it sold out in four minutes and has since been rated Best Dog Backpack by outlets like Wired, Good Housekeeping, and Men’s Health. As Bryan put it, “Money was not a thing that I really cared about, it was impact… I just need to solve a problem for me,” and it turned out to be a problem for a lot of other people too.

Takeaway: Look for a painful, personal problem you can’t stop thinking about—and build the solution you wish already existed.

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2. Overdo the Things That Matter

Bryan likes to say, “Anything worth doing is worth overdoing,” and he’s applied that to every part of Little Chonk. He binge‑learned supply chain from his wife—who ran end‑to‑end logistics at Care/of and is now Little Chonk’s COO—and channeled that obsession into building genuinely better products. When Maxine was diagnosed with arthritis, he dove into the “terrifying” world of joint health and nutraceuticals, then used what he learned to create Little Chonk’s joint supplements and clear, no‑BS education for pet parents. “I have the resources to research this, and if I’m terrified, I know for sure other people are scared shitless,” he told me, so he set out to give them peace of mind, not just pills.

Takeaway: Build your brand around integrity—over‑invest in quality, expertise, and honest education so customers feel you’re working for them, not just selling to them.

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3. Doing Good Things in the World Comes Back to You

Summary: Bryan’s most viral idea came from a constraint: Maxine was on crate rest recovering from arthritis surgery, but he still needed to make content. On a friend’s suggestion, he started taking adoptable shelter dogs out for “the best day of their life” in his backpacks, filming simple, unpolished clips with “no bells and whistles.” Those videos exploded, leading to millions of views, 23 out of 24 featured dogs getting adopted quickly, and shelters reporting “hundreds more adoptions versus last year.” In a different move, he bartered with the MTA—offering a month of pet-travel content in exchange for Little Chonk being featured across subway station screens, essentially scoring what he estimates as a “half a million to a $750,000 media buy” without spending a dollar.

Takeaway: Create ideas that are rooted in genuine care, then get scrappy about partnerships and formats that amplify that impact at scale.

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Two Free Resources to Learn More

1. Follow Bryan and Maxine on , Facebook, YouTube, and TikTok at @madmaxfluffyroad, and you can check out Little Chonk’s backpacks, leashes, and supplements at .
2. Follow these steps to get started with your own pet business or side hustle.

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One Question to Ponder

Bryan told me, “You kind of figure out what your passion is when it gets difficult—are you really up for it?” and credits his success to simply outlasting the person next to him. 

What is one thing you care about so much that you’re willing to “keep coming back over and over and over and over,” even when it stops being fun or easy?

Email your answer to howsuccesshappens@entrepreneur.com, and I’ll read some of my favorites on a future episode.

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About How Success Happens

Each episode of shares the inspiring, entertaining, and unexpected journeys that influential leaders in business, the arts, and sports traveled on their way to becoming household names. It’s a reminder that behind every big-time career, there is a person who persisted in the face of self-doubt, failure, and anything else that got thrown in their way.