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Redbud VC Mentor Monday: Kelsey Raymond

Updated: Aug 22, 2023

Kelsey Raymond started Influence & Co. with two cofounders at age 22, and over the last twelve years, has grown it to over 50 employees and 100+ clients. In 2022, Kelesy sold Influence and Co. to a holding company called Intero Digital. Kelsey has helped organize and run Startup Weekend in Columbia for seven years and has recently started angel investing in early-stage startups.

Kelsey shares with us what sketching out her company’s growth on a whiteboard looked like when having 30 employees seemed like a pipe dream, going to happy hours with coupons in tow, and the difficult decision to buy out her co-founders. Redbud VC is an early-stage venture capital fund and studio investing monetary and social capital in founders.

Share one of your favorite quotes.

“And when I'm sometimes asked when will there be enough [women on the Supreme Court]? And I say when there are nine, people are shocked. But there'd been nine men, and nobody's ever raised a question about that." - Ruth Bader Ginsburg.

During the early stages of Influence and Co., how did you effectively manage and allocate limited resources, and what creative solutions did you generate?

I remember in the early days when it was just my co-founder John Hall and I working on the business day-to-day, we talked about what it would look like if we had 30 employees and what are all the things those people would do. We literally sketched it out on a whiteboard and then divided it and said, okay, I'll handle these 15 roles, and you handle the other 15 - so we acknowledged what roles/skill-sets we WOULD need before we ever started hiring people, and that made it a lot easier to determine who and when to hire those first roles because we looked at what areas we were weakest in and knew we needed to hire a person to improve on what we could do - and that meant hiring an editor first. I think this way of thinking about hiring helped us hire the roles that made the biggest impact on us being able to focus on growth.

We also were incredibly frugal in the early days - We only ever want a team happy hour, so we had a coupon (Thank you Add Sheet!) We stayed in crappy Airbnbs and took Redeyes to save money when we had to travel for conferences, and we would write articles about the conferences to get free tickets too.

Can you recall a time when you had to make a tough decision that had a profound impact on your startup's success? How did you navigate through it?

I think the toughest decision I've had to make that made the biggest impact on our success was when I decided to buy out my two cofounders. It was all on great terms as the two other cofounders had other projects that they were focusing on. Still, it meant having to take out an SBA 7a loan, collateralized by my house and basically put all of my savings into getting the downpayment for the loan and bringing on another investor as a silent partner.

It was a tough decision because it meant accepting a LOT of personal risks, but I just kept thinking about it through the lens of what will be best for me and the employees five years from now. Well, that was in 2018, and I can say 5 years later, it is absolutely the best decision I ever made.

It meant that I had complete control over some changes I had wanted to make for a while regarding: employee benefits, flexibility, and compensation, and who was on our leadership team. We closed on buying out my cofounders in 2018, and 2019 was our absolute best year in business ever from a revenue and profitability standpoint, which was incredibly motivating to see the changes I wanted to make did result in better business outcomes.

Share your best pieces of advice for current and aspiring entrepreneurs.

Make sure you have a support group of other entrepreneurs to talk to. I have had a group of 5 business owners I meet with once a month for almost 10 years now, and I can't imagine navigating the highs and lows of entrepreneurship without them. Having a group where you can celebrate the wins and commiserate with the hardest parts of running a company is incredibly valuable to maintaining your mental health while running a company.

What are you currently reading that’s bringing great insights?

I have a 1-year-old and 3-year-old at home, so honestly am mostly reading children's books 😉 But I really enjoy the HR Brew newsletter from the MorningBrew company and Highly Regulated Newsletter from Stevie C.

The Redbud Mentor Network is a collective of successful operators, builders, and subject matter experts empowering people with their knowledge. Mentors are a keystone to the Redbud community, built on the mission to accelerate access to knowledge and network effects for founders.


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