Forbes recently published What Women Leaving Private Equity Know About Building A Business, and our CEO and Founder Kelley Williamson is one of three founders featured.
Jennifer J. Fondrevay asked Kelley how her years on M&A deal teams shaped the way she built Kelley Kouture, from the doctor's visit that ended her days in the heels she loved to the early insole flaw she refused to sell.
Forbes ran a curated selection of her answers alongside those of two other founders. With thoughtful candor, Kelley shared far more about her entrepreneurial journey than one article could hold. Jennifer asked that we publish the full Q&A below.
Original Q&A with Kelley and Jennifer
What were you doing in M&A — and what was the deal or moment that, in retrospect, planted the seed for your current business?
As women, haven't we all kicked off our shoes under the table because our feet hurt? Or
chosen flats for a big day because we knew our feet simply could not take it? For me it stopped
being a choice the day a doctor told me I could no longer wear the heels I loved.
It sounds small until it isn't. Until you realize how much of your confidence can live in something
as simple as a shoe. It is like the thing you do before a big game, the ritual that tells your body
you are ready. I could have had something custom made just for myself. But this wasn't just
about me. So many women want to feel beautiful without compromise. We deserve that.
I spent years in M&A serving on deal teams, evaluating whether businesses were truly scalable
and whether founders were ready for what private equity would actually demand of them. Then I
flipped the narrative and moved to the other side, supporting founders directly, helping them
grow well before they were ready for investment, or even if they never wanted it.
What those years taught me is that the thing that makes a business truly durable isn't the
product. It's the founder's relationship to the problem. The ones that thrive? Almost without
exception, the founder had personally felt the friction, the gap, the frustration. And they were
almost unreasonably committed to solving it because it was personal. That's not something you
can manufacture.
When I finally turned that lens on myself I couldn't unsee it. I wasn't borrowing someone else's
pain point. This was mine. And building Kelley Kouture was me finally betting on myself the
same way I had learned to bet on the founders I believed in, and still believe in.
What did you have to unlearn from your work in M&A before you could build something of your own?
I was told over and over again not to build this business. That my next career move should be
CEO of a software or business services company within a fund. Stick with what you know. I was
told that nine out of every ten footwear startups fail. Don't even try. Well what about the ten
percent who win? Why not focus on that. I stopped being willing to accept the odds as the
answer. In M&A you build toward consensus. As a founder you have to be willing to be the only
one in the room who believes in what you are building and move anyway.
I said my dreams out loud. And I am glad I did. Because the person standing right beside you
could be the very person who helps make that dream real. The people who have shown up for
this brand have moved me in ways I did not anticipate.
My chief of staff is a perfect example. I hired her because she was exceptional at process,
project management, and customer service. What I discovered afterward stopped me in my
tracks. She started her career selling shoes at department stores. Her grandfather ran the lab at
a tannery. She came to this brand knowing things about leather that most people in this industry
spend years trying to learn. She was an apprentice of leather tooling. She had built a business
in fashion accessories. And she had not worn heels in twelve years because of a foot injury.
She can now wear Kelley Kouture. I hired her because she was great. And then I learned all the
reasons she was perfect. People will surprise you if you let them.
You spent years pressure-testing other people's businesses. What did that train you to see in your own that a typical first-time founder might not catch?
Due diligence taught me to see what lies beneath the surface. Not just what a business is, but
what it can sustain. Anyone can make something look good on paper. The real question is what
happens when the pressure comes. And it always comes.
So from day one I built Kelley Kouture with both heart and structure. I think about how the
business supports itself. How resilient it is behind the scenes. What makes it truly distinct. And
how it can grow, evolve, and endure. Not just for this season but for the legacy of it.
Every morning I make a choice. What is the single most important thing that needs to happen
for this business today. Not the list. The one thing. And I do that first. Before the noise starts.
Because when you are building something this personal and this consuming, everything feels
equally important. And it is not. The ability to prioritize ruthlessly, to protect your focus and your
energy, that is the skill nobody talks about enough.
That dual lens of discipline and creativity lets me dream boldly but build intentionally. Most first
time founders lead with the dream and figure out the structure later. The structure is not the
enemy of the dream. It is what protects it.
What superpowers did you tap into as a woman starting this business? Where did being a woman serve you and where did it cost you something?
Being a woman has been my greatest advantage in building Kelley Kouture because I am the
customer. I understand her not as a concept but as a lived experience. Her desires, her
frustrations, her quiet hopes. I do not have to imagine what she needs. I have lived it. There is
something about the way women listen, the way we read a room, the way we hold space for
complexity, that makes us extraordinary builders when we trust it. She wants to feel elevated
and fashion forward without sacrificing ease of wear. She should never have to choose between
beauty and her well-being. That is the whole point.
But there have also been moments where I have had to push a little harder.
That is okay. I have learned not to fight for validation but to let the work speak. Clarity and
consistency have a way of shifting perception over time. And my superpower has always been
relationships and showing up. Even when it is hard. Even when I am scared and do not have all
the answers. Even when I am tired. I show up anyway. Because showing up is where everything
begins. The room you almost did not walk into. The conversation you almost did not have.
Opportunity does not wait for you to feel ready. It rewards the ones who show up anyway.
People will let you down. As a solo founder it lands differently than it does in a fund. What I have
learned is to move past it and focus on what you can control. Because you cannot afford to
carry disappointment for long when you are the only one steering the ship.
There is a moment early on that I think about often. We had an issue with the insoles. I caught
it. And at first the assumption was that I was a new founder with unrealistic expectations. I held
my ground. I said I would not sell the pairs with the issues. Full stop. Because my north star has
never been a tagline. It is a decision I make every single day. How does it feel on the woman's
foot. That question does not bend.
Once it became clear the problem was real they saw exactly what I had seen and moved quickly
to resolve it. It delayed delivery slightly. But I would make that same call every single time. You
cannot build trust with a woman by sending her something you know is not right. Not when the
entire promise of your brand is how it feels on her foot.
Sometimes you have to be willing to be the only one in the room who believes you are right and
wait patiently for the evidence to catch up.
What did you believe about entrepreneurship from the deal side that turned out to be wrong once you were on the other side of the table?
I thought I understood what it cost to build a consumer product business. I really did. I had sat
across from hundreds of founders. I had read their financials, walked their operations, heard
their stories. I thought I knew what it took.
I did not.
What no spreadsheet ever captured were the moments of doubt that arrive at two in the
morning when everything is quiet and the weight of it all sits with you and only you. I remember
sitting with a decision that felt impossible, and the quiet and the weight of riding on the choice I
made next. That is the moment nobody tells you about. And it is the moment that changes you.
Do you have the courage to make the tough decision.
Because that is what entrepreneurship really is. It is not a strategy. It is a daily choice. To keep
going when things feel uncertain. To trust yourself even when the evidence has not caught up
yet. And I will not pretend this has been easy. This year has tested everything I thought I knew
about resilience. It has been one of the hardest years for the footwear industry and there are
more than one brand I respect that have closed their doors. But the best time to prove you have
a winning company is to build it when things are hard. Everyone can build a business when it is
easy. The ones that sustain are built and can withstand the hard seasons.
What I also did not expect was how personal every single product decision would feel. Every
silhouette, every texture, every color is a response to something real. Something I have heard,
felt, or lived myself. That is not something any amount of market research can replace.
I had deep respect for consumer product founders before I became one. That respect has
multiplied in ways I could not have anticipated. Behind every line on a balance sheet there is a
person who made a sacrifice, took a risk, and kept going anyway. This is the hardest thing I
have ever done. And the most meaningful.
Is there a skill you were celebrated for in M&A that has gotten in your way as a founder?
Overthinking. That is the honest answer.
In M&A overthinking is not a flaw. It is a skill. You are paid to anticipate every possible outcome,
to pressure test every assumption, to find the hole before someone else does. That discipline
protects deals. It protects capital. It protects people. And I was good at it.
But when you are a founder and the decision needs to be made today, that same muscle can
work against you. I have had to learn the difference between due diligence and self doubt.
Between thoughtful analysis and paralysis. They can look identical from the inside and the cost
of confusing them is time. And time is the one thing you cannot get back.
What saved me was my other superpower. Relationships. I was the one in the room who knew
everyone, who made the introductions, who brought people together. That skill did not just
survive the transition from M&A to founder. It carried me through it. The right introduction at the
right moment has changed the trajectory of this brand more than once.
And then I had to learn an entirely new industry from scratch. Global manufacturing. The
footwear industry. I knew I wanted my shoes made in Italy because of the quality of
craftsmanship. But knowing what you want and knowing how to get there are two very different
things. I became a student again. That requires humility. And I embraced it.
Finish this sentence: The thing M&A prepared me for that nobody told me it
would prepare me for is...
Seeing the end before the beginning.
I have always been able to envision what something could become. To appreciate its full
potential, its long-term value, its place in the world. That is what years of looking at businesses
through a strategic lens gives you. You stop seeing what something is and start seeing what it
could be. You develop a kind of patience because you understand that the distance between
where something stands today and where it could stand in ten years is not a limitation. It is an
invitation.
So, I am not just building a product. I am building something that carries meaning. That is what
the K Heel represents to me. Not just a signature silhouette. A promise. That modern luxury
footwear can support the woman wearing it, beautifully and completely, without asking her to
compromise a single thing.
Every pair crafted in Italy and available at kelleykouture.com.
And I want to be honest about something else. This is self-funded, which means my family is
believing in this alongside me. That is not lost on me for a single day. So, I protect my energy
fiercely. I prioritize my health and my wellbeing as a necessity. Because I cannot show up for
this brand, for women, for my family, for the team if I am running on empty. Taking care of
yourself is not separate from the work. It is the work.
When a woman walks in wearing Kelley Kouture and tells me she feels beautiful again or
reaches for a bright joyful color for the first time in her life and wears it like a statement piece,
like a declaration of something she is finally ready to claim, whether it is her first pair or her
fourth, I know. In that moment I know I am doing something right. That is not a metric on a
spreadsheet.
That is the whole point. It has always been about how a woman feels. In the shoe, in the room, in her own confidence.
That vision has never wavered. Not once. Not through the hard seasons, not through the
moments of doubt, not through the loneliness of building something from scratch with everything
on the line. The end has always been clear. And that clarity, that ability to see it before anyone
else can, that is the greatest gift those years gave me. I just did not know it at the time.
One of Kelley's favorite styles is the "Daring", the brand's lace-up slingback that redefines the classic with edgy attitude and all-day comfort, and an adjustable lace for personalized fit. Now, you can shop the style in Leopard, one of this fall's hottest trends in luxury footwear for women. If you are waiting to follow your dreams, start. And make sure you are wearing the right shoe you want to be a bit daring too.
