Madison November 2018 Featured Entrepreneur: Diane Trim // Featured Member // Nov 13 2018

November 2018

Diane Trim of Iris Content

Doyenne Group (DG): What business do you own?

Diane Trim (DT): Iris Content

DG:What is your background? What got you to where you are now?

DT: I’m a writer and an editor. I started my career as a high school teacher in Texas, where I taught English, French and journalism. I came home to Wisconsin and taught those same subjects here, too. I left teaching to become a full-time writer and editor at Madison Newspapers (now Capital Newspapers), Epic Systems and Magna Publications. I did some freelance writing and editing on the side and I started a popular blog (now offline).

DG: What made you decide to start your business?

DT: My husband landed a position in Sheboygan and I thought I might try freelance writing and editing full time. I met my partners in an online content writing agency and we had similar work ethics and beliefs. We were dissatisfied with the agency where we worked, so we decided to form our own business. We knew that we could deliver a better product while respecting the clients and our writers. I feel really lucky. My partners and I get along really well and our aptitudes and interests complement one another. We make one another stronger and we work hard.

DG:What is your biggest accomplishment so far in life and why?

DT: My biggest life accomplishment is raising my daughter to be a happy, successful adult who is a good parent.

DG: What is your biggest accomplishment in your business and why?

DT: My biggest business accomplishment is to have a functional partnership. I know that we go further as a business because we three work together so well. We don’t always agree, but we talk and work things out. Our partnership functions better than many marriages and I know that we have something rare and precious. Nurturing this partnership is a huge accomplishment.

DG: What is the biggest obstacle that you have face while in business? What is the biggest fear that you have for your business?

DT: Our biggest obstacle is how to scale our operations. For me, it’s tough to give up editorial control because I want to make sure our product is consistently good. We work with remote freelancers who are often inconsistent workers. When we find good ones, we hold on to them with both hands and nurture them so we can retain them. We have some redundancy built into our process, but when writers or editors drop the ball, someone has to pick it up. We’re working toward the three of us partners picking up the ball less often, but we deliver client projects on time, so sometimes that means sacrifices. My biggest fear is not figuring out the scaling piece. We need to figure out how the three of us can work on growing the business more and working directly on client work less. I’m convinced the only way to work less and earn more is to expand operations and revenue streams.

DG: If you could give one quote to live by, what would it be?

DT: “I get knocked down, but I get up again/ You are never gonna keep me down” – Chumbawamba, “Tubthumping”

DG: What words of advice do you have for aspiring entrepreneurs?

DT: Don’t give up. When things look difficult, step back and think your way through the situation and plan a strategy. Don’t get mired in the day-to-day details and remember to enjoy yourself, even when the days are long.

DG: What does Madison need to encourage entrepreneurs to stay and grow their businesses?

DT: Take advantage of all of the resources available to you. There are so many in Madison, Doyenne being a big one! But also places like 100State where I work, StartingBlock, Forward Fest, Capital Entrepreneurs, Merlin Mentors, the Law and Entrepreneurship clinic and more.
Also, think hard about what your ideal work-life balance looks like, by moving away from doing client work myself, my hours have decreased but my income has increased as I’ve been able to grow our client base. How can you leverage other people and technological solutions to free up your own time? Also, consider starting your business or testing the waters as a side-gig. It can be challenging to give up the comfort and reliability of a regular paycheck, but if you can build up your product or service offering and start to build a client base before you take the plunge, it will be easier to do.

DG: What does Madison need to encourage entrepreneurs to stay and grow their businesses?

DT: This isn’t a Madison-only problem, but I think health insurance is something that holds people back from leaving their corporate jobs and jumping into entrepreneurship. The affordable care act has made it easier to get coverage but it is often prohibitively expensive. It would be great to see one of the Madison-area entrepreneurship organizations could facilitate a group-rate on insurance for solo-preneurs or early stage companies.


Join us at our monthly Connect Event on Wednesday, November 28 from 6-8pm for an evening of networking with other women professionals and a presentation from this inspirational entrepreneur.


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