What happens when a serial entrepreneur starts a brand as an outsider?
In Ben Hindman’s case, how about a lollipop company?
But not just any lollipop company.
After co-founding Splash, scaling it and then selling it, helping build Peel Insights before Shopify acquired it, and working alongside Shopify CEO Tobi Lütke, Ben decided to trade software for something decidedly more tangible.
Good-for-You Candy.
His latest venture, Le Lick, makes electrolyte-infused lollipops, aiming to bring together great taste, thoughtful ingredients, and a little more fun.
On a recent episode of Worthy for Thirty, Ben and I talked about the move from B2B technology into consumer packaged goods (CPG), how he’s approaching brand building, and why he’s embracing creativity, generosity, and vulnerability along the way.
What I appreciated most about our conversation wasn’t that Ben had figured everything out. No one does, for the record.
Quite the opposite.
He’s building something from scratch while questioning conventional wisdom, and openly acknowledging the fear that comes with it.
Here are six lessons from our conversation that I think every founder, creator, and business leader can learn from.
1. Your weirdness might be your greatest competitive advantage
There’s no lack of advice unsolicitedly telling entrepreneurs to study competitors, follow best practices, and build what the market wants.
And there’s value in all of that.
But what happens when everyone follows the same playbook?
You end up with a lot of sameness
Ben has spent much of his career doing the opposite.
From his early days creating unconventional experiences to building Splash and now Le Lick, he credits much of his success to having the freedom to be himself.
He recalled something a former boss at Thrillist once asked him when reviewing an event concept:
“Where’s the WTF factor?”
The idea was simple. What makes this experience so unexpected that it leaves an impression compelling someone to tell someone else?
That philosophy pervades Le Lick.
Instead of launching the brand with a set of three flavors industry experts recommended, Ben launched with six and quickly added more.
Instead of coloring the candy itself, Le Lick uses colored sticks.
And instead of building a traditional wellness brand, he’s leaning into humor, unusual flavors, and even a custom lollipop designed to get Skrillex’s attention.
Some of these ideas might sound ridiculous.
That’s partly the point.
The takeaway: Differentiation doesn’t always require a breakthrough technology, idea, or an enormous marketing budget. Sometimes it starts with having the confidence to create something that doesn’t look like everything else.
For founders, the question is worth asking:
What are we doing that people will actually remember?
2. Creativity isn’t reserved for the ‘creatives’
I asked Ben a question that I think gets overlooked in business.
Can anyone be creative?
His answer was a quick ‘yes.’
He shared the story of a business he once experimented with called Don’t Paint the Walls.
The concept involved putting people in hazmat suits, handing them paintbrushes, turning on music, and encouraging them to go wild.
What he discovered was that people weren’t necessarily lacking creativity.
They were afraid of outside opinions.
They were concerned about whether they were good at painting or whether their work would look right.
Remove that pressure, and people started creating.
Ben also made an interesting observation about his finance lead, whom he described as incredibly creative with spreadsheets.
I loved that example.
Because creativity isn’t assigned to a job title.
It’s the operations leader who finds a better process.
The finance executive who solves a problem differently.
The founder who sees an opportunity in an overlooked category.
The takeaway: One of the most important things a leader can do is create an environment where people feel comfortable experimenting without worrying about looking foolish.
If every new idea needs to be perfect before someone shares it, how many good ideas never see daylight?
3. Trust your taste, but be open to customer feedback
One of my favorite moments in the conversation came when Ben talked about working at Shopify.
He recalled watching CEO Tobi Lütke make creative decisions based on something surprisingly simple.
His gut.
Even while leading a company with thousands of employees, Tobi was willing to weigh in on something as seemingly small as a color choice.
What impressed Ben wasn’t the decision itself.
It was the confidence behind it.
The willingness to trust his judgment.
Ben has carried that lesson into Le Lick.
When developing an orange coconut lollipop, the team went through 26 rounds before settling on the final flavor.
They gathered feedback, experimented, and refined the product.
But eventually, someone had to make a decision.
Ben trusted his taste.
Interestingly, he doesn’t apply that same judgment to every flavor.
He doesn’t particularly love watermelon, so he gave someone on his team ownership of developing it.
That’s an important distinction.
Trusting your instincts doesn’t mean assuming your preferences are universal.
It means knowing when to make a call and when someone else has a better perspective.
For business leaders, this is especially relevant today. Be self-aware.
We have access to more customer data, competitive intelligence, and market research than ever before.
All valuable tools.
But data doesn’t eliminate the need for judgment.
The takeaway: Listen to your customers, gather the evidence, and empower people with different perspectives. Then be willing to make a decision.
You can’t outsource every creative choice to a survey.
4. Your customers might value something completely different than what you’re selling
Here’s a lesson that every founder and marketer should pay attention to.
When Le Lick first entered the market, much of its marketing focused on functional ingredients.
Electrolytes. Sugar content. What made the product different from conventional candy.
Those seemed like obvious selling points.
But as customers started buying and coming back, Ben noticed something.
They weren’t necessarily returning because of the functional benefits. They were returning because they loved the taste.
That epiphany compelled the company to rethink its messaging.
Instead of leading with ingredients and nutritional details, Le Lick began emphasizing flavor and the experience of enjoying the candy.
The functional benefits were still there.
They just weren’t necessarily the primary reason people fell in love with the product.
This is such an important lesson for anyone building a business.
Founders spend months or years developing products. Naturally, they become attached to the features that make those products special.
But customers don’t always care about the same things.
A founder might sell efficiency.
The customer might buy peace of mind.
A software company might promote its features.
The customer might simply love how easy it is to use.
A candy brand might promote electrolytes.
The customer might just want something that tastes delicious.
The takeaway: Pay attention to why customers return, not just why you think they should buy.
That distinction can change your marketing, positioning, and even your product roadmap.
5. Giving back doesn’t have to wait until you’re successful
This part of the conversation felt especially relevant to what we’re trying to explore on Worthy for Thirty. Sounds very Kyle Gordon-esque.
Ben believes generosity should be built into how Le Lick operates, not something the company considers after it reaches a certain revenue milestone.
During our conversation, he shared that Le Lick had given away approximately 14,000 lollipops in the previous month.
Some went to events. Others supported meaningful causes, including care packages for people dealing with illness or recovering from breast cancer.
And yes, giving away candy can also be good marketing.
Sampling allows people to experience a product they might otherwise overlook.
Ben doesn’t shy away from that commercial reality.
But he also genuinely enjoys giving.
That’s part of who he is, and he wants it reflected in the company he’s building.
What made the conversation particularly interesting was his willingness to acknowledge the tension.
He admitted the company had given away too many lollipops that month relative to its finances.
That’s a real challenge for an early-stage business reinvesting its money into inventory.
Generosity carries a P&L implication.
So how do you build a business where giving is sustainable?
Ben is still figuring that out. Just like we all are :).
He’s working to measure the impact of sampling while remaining committed to the belief that generosity can be good for people and good for business. At the same time.
The takeaway: You don’t need to wait until your business is wildly profitable to make a positive impact.
But if giving is central to your mission, you also need to run the numbers and run an economic model that supports it.
Purpose and profitability aren’t competing ideas.
The challenge is designing a business where they can reinforce each other.
6. Experience doesn’t eliminate founder fear
This might have been the most relatable part of our conversation.
Ben has built businesses, experienced exits, worked alongside accomplished entrepreneurs, and navigated the ups and downs of startup life.
You might assume that starting another company would feel easier.
That experience would replace uncertainty with confidence.
But Ben admitted something that doesn’t always make it into curated founder story reels we see on Instagram.
He still feels afraid.
Afraid that the business won’t work.
Afraid that something he’s poured himself into could disappear.
And sometimes frustrated that, despite everything he’s learned, fear remains such a powerful emotion.
I appreciated his vulnerability.
Because it’s easy to confuse entrepreneurial optimism with an absence of doubt.
They’re not the same thing.
Ben described what he calls delusional optimism as being able to see around the next corner without necessarily knowing what’s waiting three corners ahead.
You keep moving anyway.
You trust your experience, your team, and your gut.
And you learn to make decisions without having every answer.
That’s entrepreneurship.
The takeaway: Confidence isn’t knowing that everything will work out.
It’s being willing to keep building when you don’t know.
For founders and leaders, the goal shouldn’t necessarily be to eliminate fear. It’s to avoid letting fear dictate every decision.
What Ben’s journey teaches us about building a business today
There’s something fascinating about watching an experienced technology entrepreneur enter the CPG industry.
In software, you can change a feature, update a website, or test a new experience relatively quickly.
In consumer products, you’re dealing with so many moving parts: manufacturing, physical inventory, ingredient costs, packaging, and margins.
Mistakes can be expensive.
And unlike software, you can’t simply push an update to a lollipop.
Ben is learning those realities firsthand.
He’s working to reduce production costs, understand customer behavior, build brand awareness, and figure out how to scale without sacrificing what makes Le Lick different.
But he’s also bringing lessons from his technology career into an industry that operates very differently.
Experiment quickly.
Listen to customers.
Make memorable experiences.
Trust your team.
And don’t lose the personality that made people pay attention to your brand in the first place.
That combination is what makes his story so interesting.
He’s not just trying to build another candy brand.
He’s exploring whether a company can be commercially successful while staying playful, unconventional, and generous.
And he’s doing it without pretending to have everything figured out.
The question I’d leave founders with
After speaking with Ben, I kept coming back to one thought.
What would you build differently if you weren’t so worried about what everyone else thought?
Maybe you’d finally launch the product you’ve been sitting on.
Maybe you’d stop copying competitors and develop a brand that actually reflects your personality.
Maybe you’d give your team more room to experiment.
Or maybe you’d build generosity into your business now, rather than waiting for some future milestone.
Whatever it is, there’s something worth learning from Ben’s willingness to embrace the uncomfortable parts of entrepreneurship.
The uncertainty.
The creativity.
The weirdness.
And the vulnerability that comes with putting something new into the world.
Because the businesses we remember aren’t always the ones that followed the rules most closely.
Sometimes they’re the ones brave enough to create their own. Uber comes to mind.
Listen to the full conversation
In my conversation with Ben Hindman, co-founder of Le Lick, we explore entrepreneurship, building a CPG startup, consumer brand marketing, creativity, founder fear, and what it really takes to do good while doing well.
🎧 Listen to the full episode of Worthy for Thirty on Spotify, Apple Podcasts, or wherever you enjoy podcasts.
Explore Le Lick:
https://enjoylelick.com
Worthy for Thirty features conversations with founders, business leaders, and changemakers proving that doing good and doing well can be part of the same equation.
If this resonated, share it with a founder or creator who could use a reminder to trust their instincts and keep building.