Where Courage Meets Canvas: The51 Art & Investment Retreat
What three days of painting reminded me about investing, conviction, and believing before you have proof.
A perspective from Shelley Kuipers, Co-founder & CEO, The51
A Weekend Built on Two Kinds of Risk Taking
Women joined us from across Canada for three days in Victoria, BC that felt less like something formal and more like a reset.
We painted in the most beautiful garden studio. We were nourished with beautiful food. We moved through yoga one morning. And to close out the weekend, we sat with Leah Bennett as she shared her perspective on investing in art, a lens most of us had never applied that seriously before.
Laura and I conceived of this retreat together as an opportunity for The51 to do something quite different.
I had experienced one of Laura’s retreats in the past, and I knew how awakening it could be. I wanted to share some of that experience with The51 community: the chance to step outside the environments we typically associate with investing, business and leadership and see what might emerge when we made room for something else.
What I didn’t know was how differently this weekend would unfold from what Laura and I had imagined.
Meet Laura, and an Unexpected Turn
We gathered at the home, gardens, and studio of artist Laura Harris on Vancouver Island.
Laura has spent more than twenty-five years building a following as a painter and creative, with work held in corporate collections including The Ritz-Carlton, Mercedes-Benz, and The Keg, and features in Chatelaine Magazine and Christie’s Luxury Home Magazine.
Her canvases are exuberant, sensual, and often large in scale, built through an intensely physical process of dripping, brushing, and throwing paint, usually with music playing loudly.
She works out of a cottage studio just twenty feet from her house, reached through French doors and past a pond: the kind of space that makes you want to slow down the moment you step inside.
It’s easy to see why she wanted us there.
She had hoped as much herself.
“I hope our home, the gardens and the studio do some of that work for me,” she wrote to us. “I hope they wrap themselves around you a little, and that you feel completely at home.”
Laura had planned to paint alongside us herself that weekend.
Life had other plans.
On the morning of the retreat, Laura’s father took a sudden, serious turn, and she needed to be with her family instead of with us.
“My dad has been in ill health for some time now,” she wrote to us that morning. “Although we knew this season was coming, things changed quickly, and he took a significant turn yesterday. Today my place is beside him and alongside my family.”
As for who would be looking after us in her place, she had already taken care of that.
“Michelle is an extraordinary woman and artist and one of the finest teachers I know,” she wrote, “bringing more than thirty years of experience, wisdom and encouragement to the easel.”
Of Alice, Rachel, Sue, and Pete, she was just as certain.
“They are my people,” she wrote. “Between us we have been cooking, gathering, hosting, laughing, problem solving and creating a little magic together for more than fifteen years now, and there is nobody in the world I trust more.”
Michelle Miller stepped in to lead the easel work, and the crew Laura described — Alice, Rachel, Sue, and Pete — quietly made sure the three days felt effortless, even though pulling off a weekend like this never actually is.
The51’s own Alice Reimer traded her seat at The51 table for an apron and spent the weekend running the kitchen with Rachel. “Chef Alice” kept us fed with food every bit as thoughtful as the art on the walls.
And on one of the mornings, despite everything she was carrying, Laura slipped quietly into the studio just to say hello.
We did what a room full of women held so generously by her would do. We wrapped her right back up in it, in hugs, in thank yous, in the kind of love that did not need explaining.
That moment has stayed with me.
So did something Laura had left us with in her note before she disappeared that first morning:
“Artists and investors actually have more in common than we might think. Both ask us to believe in something that does not yet exist. Both involve risk, uncertainty and optimism. Both require us to trust our instincts, do something that scares us a little, and move forward before we know exactly how things are going to work out. And more often than not, what waits for us on the other side is better than we could have imagined when we began.”
Putting Conviction into Practice
Over the next few days, we got to experience what Laura meant.
There is something vulnerable about standing in front of a blank canvas, especially when you don’t consider yourself an artist. There is no spreadsheet telling you what to do next. No certainty about what the finished product will look like. At some point, you simply have to put paint on the canvas.
You make a choice. You respond to it. You keep going.
It struck me how familiar that feeling is.
So much of investing asks us to evaluate what is already there: the evidence, the numbers, the market, the risks. But ultimately, investing is also an act of imagination. We are developing conviction about something that is not yet fully realized and deciding whether we believe enough in what could exist to move forward before we know exactly how things are going to work out.
By the time we reached our final session of the retreat, that connection between art and investing had started to feel much less theoretical.
Collecting with Conviction
If painting was where we let go, Leah Bennett’s session, our final session of the retreat, was where we leaned back in.
Leah, a friend of The51, is Chief Investment Strategist at Concurrent and President of Elevate Family Partners, with more than 30 years of experience in asset management, wealth strategy, and financial leadership.
She has built a career evaluating risk, value, and long-term stewardship, and now applies that same discipline to the art she collects.
Leah’s talk centered on a philosophy she calls Collecting with Conviction.
Her core message: buy what you love, but don’t stop there.
Three ideas from her presentation stayed with the room:
Passion first. “Before buying, ask: does the work move you? If not, don’t buy it.” A collection built to chase trends rarely holds up, financially or personally.
Stewardship, not just ownership. Leah described herself as a steward rather than an owner of the works she collects, lending pieces to museums so the art, and the conversations it starts, can reach further than her own walls.
Research as discipline. Passion gets you in the door, but understanding an artist’s career trajectory, institutional support, and long-term significance is what protects both the cultural and financial value of a collection over time.
She distilled all of it into one model: a lasting collection sits at the intersection of personal conviction, institutional validation — are museums collecting and exhibiting the artist? — growing collector demand from serious collectors and institutions rather than speculation, and artistic excellence.
Gallery representation matters too, since strong representation often signals long-term career development for an artist.
But the line that landed hardest for me was this: “As collectors, we have the ability, and perhaps the responsibility, to elevate artists whose stories deserve to be told.”
Art as activism, not just acquisition.
I suspect The51 will be collaborating with Leah again in the future. I can’t wait to see what that looks like, particularly as we continue exploring the intersection of art and investment.
What the Weekend Left Me Thinking About
By the time we left Laura’s studio, it was hard not to notice how neatly the weekend’s two threads — painting and investing — had tied themselves together, almost exactly as Laura predicted in her letter to us.
We spent three days doing something a little uncomfortable: putting brush to canvas without knowing what would come of it and hearing a serious case for art as an asset class, many of us for the first time.
Both asked the same thing of us: a willingness to trust the process before we could see the outcome.
What I didn’t expect was how everyone would leave.
Women who had never picked up a paintbrush walked away holding canvases they were genuinely proud of, more than a few of them stunned that they’d made something so alive.
Conversations that started side by side at an easel turned into real friendships, with people already making plans to see each other again.
And across the board, people left rested in a way that’s hard to come by: inspired, a little lighter, and already asking when the next one is.
I keep coming back to what Laura wrote about artists and investors believing in something that does not yet exist.
The best investing, I think, requires more than being able to evaluate what is already in front of us. It asks us to imagine what could exist, to develop conviction about a founder, an idea, an opportunity or a future that is still being created, and then decide whether we are willing to help make it real.
There is risk in that. There is uncertainty. And, as Laura reminded us, there is optimism.
Maybe that’s why putting a paintbrush in the hands of a room full of investors felt so unexpectedly fitting.
That’s the retreat, in one sentence: a room full of women who came from across the country and left having learned that courage and conviction, whether you’re holding a paintbrush or building a portfolio, look a lot more alike than we tend to think.
“You’re going to have a beautiful day,” Laura had told us in her note, before any of us had even picked up a brush.
She was right.
To everyone who joined us on this retreat: thank you. You inspired us. You were awesome, every one of you.
And to Laura: thank you for trusting us with your home, your people, your practice, and ultimately with an experience that became something different, and perhaps even more meaningful, than any of us had planned.
With thanks to the friends and partners who filled our retreat gift bags with such care: Simons, Radford, Nala, Elate Beauty, Dean Davidson, Mave & Chez, & Blume.
Laura’s available work can be viewed and purchased through Gallery Merrick, and she also welcomes commissions.
— Sincerely, Shelley Kuipers, Co-Founder & CEO, The51
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