Meet Kelsey Raymond: Entrepreneur, Investor, and Missouri Startup Weekend Mentor

Kelsey Raymond’s entrepreneurial journey started earlier than most. Before she co-founded a multi-million dollar content marketing agency, led a major acquisition and merger, and became COO of a 300+ person global firm, she was just a kid knocking on doors—selling painted rocks and homemade dog bandanas to her neighbors.

“I loved the fun of creating something and putting it out into the world for others,” she says. “But what really solidified my passion for entrepreneurship was participating in Mizzou’s Entrepreneurship Program and getting mentorship and coaching from so many great local entrepreneurs during my four years there.”

That passion led her to co-found Influence & Co., which quickly became a leader in content marketing. By 2018, Kelsey was at a crossroads. She had spent years building Influence & Co., but if she wanted to continue growing it on her terms, she needed to take a risk.

So she did.

She took out a multi-million dollar SBA loan to buy out her co-founders, securing an 88% ownership stake in the company—personally collateralized. It was a gamble, but it paid off in every way.

“I went from getting 6% of our profit share, but not actually being an equity owner, to owning 88.75% of the business, and having the weight of a multi-million dollar SBA loan to go with it,” she says.

That decision shaped everything. With full autonomy, she restructured the company, implemented more progressive benefits, and set the business on a path that ultimately led to a sale and merger with Intero Digital in 2022. Now, as COO of Intero Digital, Kelsey is scaling a global marketing powerhouse. She’s also an angel investor focused on supporting women-led startups, a decision sparked by one statistic:

“In 2023, startups founded exclusively by women received approximately 2% of total VC funding in both the United States and Europe. That is absurd. Full stop. It needs to change, and I wanted to be a very small part in changing it.”

Now a 2025 MOSW mentor, she’s bringing her experience as a founder, investor, and executive to Startup Weekend—coming full circle from when she helped launch the first Columbia Startup Weekend over a decade ago.

Q&A with Kelsey Raymond

What lesson(s) stand out from acquiring a majority stake and evolving Influence & Co.? Too many lessons to count, but here are a few I learned the hard way:

• Solidify ownership agreements at the start—not once the company is already making money.
• Be overly transparent about the hard parts of a job during recruitment. We made hiring mistakes by focusing too much on the fun part of the job while downplaying the realities of client work, including its ups and downs.
• Don’t be scared to raise your prices if you’re providing great service. Every single time I’ve worried about raising prices, it’s made no difference. If you’re delivering an exceptional product, charge what it’s worth—people will pay.
• Treating employees with respect and dignity is a good business decision. It builds goodwill, and that comes back tenfold.”

What do you remember about the first Columbia Startup Weekend? My most vivid memory is me and Alyssa Patzius eating pizza at 2 a.m. at Museao, watching Modern Family on a projector while developers coded through the night.

My other memory? People being rude to Alyssa after she personally cleaned the men’s bathroom because it got so gross after one day.

So here’s a shoutout: THANK YOUR VOLUNTEERS. THEY ARE DOING IT FOR FREE.

What’s one common marketing mistake you see founders make, and how can they avoid it? People being scared to share their idea. They think if they talk about it too much, someone will steal it. That’s the opposite of how you should think. Instead, tell literally everyone you meet about your idea. Validate it through potential customers, investors, employees, etc.

If you could give one piece of advice to founders about scaling a business the right way, what would it be? Assume you might get hit by a bus tomorrow. Do people know what to do? You need a ‘hit by a bus’ document. Prioritize documentation and processes before you scale, or you’ll hit a wall.

If you could go back to the first Columbia Startup Weekend, what advice would you give yourself? Get at least one hour of sleep over the weekend so you don’t end up with stress-induced shingles afterward.

What’s one book, podcast, or resource that every founder should check out? Radical Candor by Kim Scott—the only leadership book I ever recommend.

If you could instantly master any skill, what would it be? AI prompt engineering, so I can have a job when the robots take over.

What’s your favorite way to unplug from work? Long walks with a podcast or tickle fights with my toddlers.

You get to have dinner with one entrepreneur, living or dead—who is it and why? Beyoncé. And the why? Because Beyoncé.

What excites you most about Missouri Startup Weekend this year? I get so much energy from hearing people’s new ideas—I’m just excited to listen to pitches!

Any final words of encouragement for participants? Don’t be the person who leaves because your idea didn’t get chosen. You WILL learn something, and you WILL have fun. Enjoy the process.