Burn the Playbook: How Kate Wolff Built Four Companies, Raised Millions, and Rewrote the Rules
Kate Wolff
“The number one qualification for doing any of this is being comfortable in the uncomfortable. That is where the real leadership, and real payoff, lives.”
Kate Wolff did not plan to become a serial entrepreneur. She did not map out a four-company strategy or prepare a pitch deck before leaving her job. She walked away from a successful career in big agency advertising because she saw too many limits. She wanted to do more, create differently, and build something where she could be her full self. What happened next was not a pivot. It was a complete redefinition of what leadership, creativity, and business could look like.
In this episode of the Badass Women in Business podcast, Kate takes us inside the journey of launching Lupine Creative, No Sheep Studios, Do the WeRQ, and LumiTerra. She tells the truth about launching a business just before the world shut down, raising capital in the middle of a trade war, and why being a founder means being deeply uncomfortable most of the time. What she offers is not a startup success story. It is a deeply honest look at what it takes to build and lead without losing your voice.
From Holding Company to Building Her Own
Before Lupine Creative, Kate spent years climbing through the ranks of major agencies like Publicis, DDB, and TBWA. She did the client work. She did the strategy. She touched nearly every department in the house. Most people told her that was a mistake. Agencies prefer specialists. They want you in one box.
But Kate wanted more. She liked the doing. She loved the building. She thrived in the mix of new business, creative insight, and hands-on production. No single role could contain all of that. The agency model was not built to allow it. So she left.
What she did not leave behind was her creative muscle or her deep understanding of how culture, identity, and message move together. She started Lupine Creative as an experiential agency just weeks before the COVID shutdown. Overnight, the plan collapsed. No events. No activations. No clients ready to play in public spaces.
She could have quit. Instead, she pivoted. Fast. Lupine moved into digital campaigns, brand partnerships, and video production. Kate learned to fail fast, rebuild quickly, and adapt without ego. That agility became the backbone of everything that came after.
Why One Business Was Not Enough
Most people would have focused on saving the one company. Kate built three more.
First came No Sheep Studios, a full-service production house that supports Lupine’s creative work. Then came Do the WeRQ, a nonprofit collective pushing for LGBTQ+ representation in advertising and media. Then came LumiTerra, a product company focused on replacing single-use plastic cups with aluminum alternatives.
Each of these businesses came from a need, not a business plan. No Sheep allowed her to own the execution side of creative. Do the WeRQ began as a conversation with a fellow queer leader about the lack of community and data around LGBTQ+ professionals in advertising. LumiTerra came from her firsthand experience watching trash pile up at brand events and asking what a better solution could look like.
The common thread between all four? Culture. Sustainability. Visibility. Integrity. And a refusal to do business as usual.
The Hardest Year That Built the Strongest Foundation
Launching a business in February 2020 was brutal. Kate lost her life savings. She had no roadmap. But she did have freedom. With no team to manage in those early days, she could turn on a dime. She built what the market needed, not what she had originally planned.
In hindsight, she sees this as a gift. Had Lupine stuck to its original vision, it would be just another experiential agency. Instead, it evolved into a nimble creative partner known for its 360-degree campaigns, social-first work, and thoughtful brand collaborations.
Failure made the company stronger. It made her leadership sharper. And it taught her the difference between being excited about ideas and being committed to outcomes.
Building a Team of Builders
Lupine is not for everyone. Kate is clear about that. She tells candidates exactly what the work is and what it is not. You will not be on camera. You will be behind it. You will not coast. You will build. You will not get by on good vibes. You need to love the craft.
She looks for “delightful weirdos”—people who want to make something out of nothing and take joy in the creative process. Her interview questions are specific. What part of the work brings you joy? What kind of joy sticks with you? What kind of work gives you energy instead of draining it?
She is not interested in scale for its own sake. She is interested in building a culture of people who care deeply, work hard, and create things that matter.
And when someone is not a fit? She lets them go. Fast. As she says, the worst thing a leader can do is fail slowly.
Do the WeRQ: Queer Visibility as Infrastructure
Most companies do not track LGBTQ+ data. Until recently, they did not have to. Until 2021, queer people were not even federally protected. Why would someone disclose their identity in a workplace that could fire them for it?
Kate and her co-founder Graham Nolan created Do the WeRQ to change that. The organization runs quarterly research, supports ERG programming, develops mentorship networks like Project Violet, and builds toolkits that help companies move from performance to real inclusion.
The goal is not to be a Pride Month initiative. The goal is to change how the industry functions.
They are also preparing to launch a major national survey that will finally give real data on queer representation across media and marketing. Because visibility should not be anecdotal. It should be measurable.
LumiTerra: Brand Meets Product
Launching a product is a different game. But Kate’s branding background gave her a huge edge.
Most founders burn through capital on bad marketing decisions. They hire the wrong people, tell the wrong story, or try to design by committee. Kate used her Lupine team to build LumiTerra’s visual identity, brand strategy, pitch decks, renders, and website. That alignment made the company investor-ready from day one.
She even built a new low-cost offering inside Lupine to help other early-stage companies with mission-driven products. It is called Widget Work. If your company has a for-good element, addresses a marginalized community, or comes from one, Lupine will help you bring it to life without draining your budget. It makes her team happy. And it helps more founders get a fair shot.
Raising Capital Without Losing Yourself
Closing a Series A is no small thing. Doing it during a global trade war as a company that relies on aluminum? Even harder.
Kate does not romanticize the fundraising process. She calls it what it is: compromise. No one gets everything they want. The key is to enter the room already knowing your non-negotiables. What are you willing to give up? What will you protect at all costs?
And if you are not prepared to be told no, often and without explanation, you are not ready to raise. You need to sit with rejection, discomfort, silence, and self-doubt. Not once. Constantly. That is the work.
What made it bearable for Kate was knowing that she had built something real. When investors said yes, it was not to a pitch. It was to a product. A brand. A mission.
The Real Cost of Building Something
People love the highlight reel. But Kate insists on telling the whole story. The skipped vacations. The unpaid weeks. The anxiety. The loss. The exhaustion. The joy that only comes from pouring everything you have into something that might not work—and then watching it grow anyway.
She does not believe in work-life balance. She believes in balance. Some things fill you. Some things drain you. The goal is to know the difference and structure your life accordingly.
For her, that includes 80-hour weeks, a partner who gets it, and a team that makes the work worth it. It includes date nights, inbox marathons, whiteboards full of wild ideas, and the quiet satisfaction of knowing you are building something that did not exist before.
Advice for Founders, Creators, and Builders
If you are thinking about starting a company, Kate has a few things to say:
Know where your revenue is coming from before you start. If you do not know how you will make money, you do not have a company.
Get ready to work harder than you ever have. If you do not like the work, do not build the business.
Build systems that do not depend on one person’s drive. ERGs should not collapse when one person quits.
Hire people who love the craft, not just the idea of the title.
If you want to serve the queer community, you need to prepare for backlash. Not as a possibility. As a certainty.
Show up with your full self, or do not show up at all.
Culture Is the Point
Kate believes queer people have always made culture. Ballroom in the 80s. Slang that shows up in your inbox a decade later. Performance, style, language, and vision that begins on the margins and becomes the center.
Her work is not about chasing trends. It is about honoring the creators behind them. Her companies are not built to fit inside a mold. They are designed to break it.
The future, she says, will be built by people who are willing to imagine something that does not exist yet. But imagination needs space. Digital overload, aesthetic sameness, and algorithmic feedback loops can kill new ideas before they form.
Kate’s mission is to hold space for that creativity. To fund it. To protect it. To build the scaffolding so the next generation of builders can take it even further.
Last but not Least
Kate Wolff is not trying to be a role model. She is trying to build things that last. The work is real. The impact is measurable. The leadership is intentional.
She is not interested in status. She is interested in scale that matters.
If you are dreaming about starting something, ask yourself this: Are you willing to sit in the discomfort long enough to see it through? Can you hold the hard without flinching? Can you build without needing applause?
If the answer is yes, start building.
And if you need a playbook, burn the old one. Kate already did.
