Henrik Werdelin

BarkBox wasn't a stroke of genius — it was 'the least shitty idea of the day'

Henrik Werdelin, co-founder of BarkBox/Bark, debunks the heroic-origin myth. The Disney-for-dogs subscription box started as a casual Friday brainstorm; they didn't think it would be a big business and only realized it was working once traction showed up.

“I think when you build a big business like we have now, you want to try to come up with these glorious stories about like how insightful you were. It wasn't really a big deal. Like, I think it was kind of like the least shitty idea of the day. We definitely didn't think it would be a big business. I think what we saw pretty quickly was that it was working.”

Anchor the business in a promise, not a product

Werdelin explains why he modeled Bark on Disney: Disney is hard to peg because it makes toys, parks and content, yet it's coherent because it's anchored in a customer promise. He built Bark around the promise of dog happiness rather than any single SKU.

“And so I think what was intriguing for a slightly kind of neurotic entrepreneur like myself was this idea that you could anchor your businesses not in a product that you were making, but in a promise or a problem you were solving for your customer. And we wanted to make our dogs happy.”

Steal thisAnchor your brand in the customer problem or promise you solve, not the product you ship — it lets you expand into new lines without losing coherence.

Success is obvious fast; failure is the opaque one

Werdelin's heuristic from starting several companies: if customers genuinely care about a product, traction shows up quickly and success is fairly obvious early. It's the unsuccessful ideas that stay ambiguous and tempt you to keep going.

“And in many ways, I feel now that I've started a few things, success kind of like is somewhat obvious pretty quickly if you have a product that customers really care about. And it's a little bit more like the unsuccessful stuff that's a little bit more opaque.”

Steal thisDon't agonize over whether a new product is working — real traction is obvious fast; if it stays ambiguous, treat that as a signal to kill it.

Sell the lifestyle, not the product (the MTV playbook)

Drawing on his MTV background, Werdelin made Bark's content about the dog-owner lifestyle ('what do you do if your dog doesn't like your boyfriend') rather than utilitarian product copy. They even trolled political forums posting from a dog's point of view to build a culture of playfulness people wanted to share.

“I think our content would be more about like, what do you do if you're dog doesn't like your boyfriend, then it was about like 5 ways to clean the paw of your dog. And I think everything, things tend to be pretty utilitarian because most product owners or entrepreneurs were like, well, I need to sell my stuff.”

Steal thisMake your content about your customer's lifestyle and identity, not your product's features — it's more shareable and easier to associate with.

He bribed an engineer and hijacked MTV Australia at 2am

Early in his career Werdelin pitched a UGC-style web/TV show idea that MTV engineers dismissed as impossible on a Windows 95 machine. So he bribed the transmission engineer, discovered the offices were wired for broadcast, and went live at 2am without permission — turning the stunt into a job running product development for all MTV channels outside the US.

“So I got a little bit stubborn and figured out that all the offices was wired for broadcast. And so I bribed the transmission engineer and I went live at 2 in the morning from my studio without permission. And so back in the days, that didn't kind of land you in jail at MTV.”

Try many crazy things, then kill them ruthlessly on 'data day'

Bark's operating rhythm: build whatever idea they want, run it for a week, then on Sunday 'data day' Matt reviews the numbers and rolls back the entire week if metrics dropped. Werdelin calls it a 'bipolar' attitude — don't overthink experiments, but be disciplined about killing the losers fast.

“And so in the early days, we would build whatever we wanted to do, and then we would run it for a week. And then on Sundays, Matt would do data day. And if we had kind of dropped in numbers, we would just roll back a whole week.”

Steal thisRun new experiments for one week, then hold a weekly 'data day' to roll back anything that didn't move the numbers — fast to try, fast to kill.

Pay influencers on a fixed CAC — only for converted subscribers

Bark's discipline around influencer spend: stick to a target customer-acquisition cost (CAC) and, in the early days, pay celebrity dogs only when they converted a sale, roughly $20–$30 per subscriber. Werdelin notes the model has since shifted to more pay-to-play.

“But we've always been pretty disciplined by having a CAC that we stick to. So I would imagine it was like within those, I don't know what it was back then, like $20 or $30 or whatever it was, that we would offer these celebrity dogs if they converted into a sale.”

Steal thisPay influencers on conversion against a fixed CAC target, not flat fees — so acquisition spend stays tied to real subscribers.

He reverse-engineered eHarmony data to find his wife

Single and wanting to settle down, Werdelin studied relationship-longevity research and eHarmony's published data, then defined 30–40 properties that would raise the odds of a lasting match. Concluding similarity beat compatibility statistically, he used 'serendipity' (friends-of-friends) as a proxy for chemistry he couldn't measure on paper.

“So I started to study all the books I could find about relationship therapy and longevity in relationships and start to try to understand, well, what is actually the background kind of for all these dating algorithms?”

Engineer serendipity, then let fate take over

Shaan distills Werdelin's dating approach into a transferable framework: don't reduce big life decisions to a rigid checklist, and don't leave them fully to chance. Do the work to put yourself in high-probability situations, then let real connection happen.

“You engineered serendipity, right? You did some work, but then you let real life take over and fate take over in a way where you said, you know, I don't know who I'll meet. I don't know who I'll connect with, but I'm just gonna put myself in positions where maybe I can increase the sort of odds of getting lucky.”

Steal thisFor big life decisions, engineer serendipity — put yourself in high-probability environments rather than relying on a rigid checklist or pure luck.

The 8+1 framework: eight life boxes plus the box for thinking

Werdelin runs his life on an '8+1' grid borrowed from a Dan Shipper write-up: Transact, Invest, Assist, Learn, Health, Family, Relationship, and Ego/self-kindness. The crucial ninth box is reserved for actually spending time thinking about all the others.

“So I have this thing I call the A+1 framework. And the A+1 framework is really about the core elements that I'd like to kind of like be quote unquote successful people in.”

Steal thisMap your life onto fixed boxes (money, investing, helping, learning, health, family, relationships, self) and reserve a dedicated ninth box just to think about them weekly.

Run growth-hacker experiments on your parenting

Werdelin applies experiment-logging to family time: bored building the same blocks with his son and reaching for his phone, he logged 'play experiments' in Airtable, bought a tabletop ping-pong table, and replaced the bad interaction with one they both loved.

“And so something as simple as, oh, you know, when I was about 5, I thought to play ping pong. So I bought a ping pong table, right? Like a little thing that you put on top of your dining table. And so next weekend, I then, again, because I'm slightly crazy, I put in my little Airtable of my experiments. And then I went down to try that and he loved it.”

Steal thisTreat personal life like a growth funnel — log small experiments (even for parenting) and keep the ones that produce a better outcome.

Overlap your life boxes to beat work-life balance

Werdelin's answer to balance: stack categories so one activity hits several. Working with friends gives you 'relationship' plus 'transact'; founding a company gives 'transact' plus 'invest' (salary plus equity); a walking business meeting in San Francisco adds 'health.' Sometimes the move is instead to separate boxes — e.g., keep a good-paying job and invest the surplus rather than taking equity risk.

“You get relationship and you get transact, right? You know, sometimes if you start your own thing, you get transact and invest, right? Because you often make both some salary and you have some stock options.”

Steal thisStack life priorities into single activities — work with friends, take walking meetings, found a company for salary plus equity — so you advance multiple boxes at once.