Generic selectors
Exact matches only
Search in title
Search in content
Search in posts
Search in pages

Real Talk With Kristy Dickerson and Jenny Grumbling, Founders of STARTplanner

Real Talk With Kristy Dickerson and Jenny Grumbling, Founders of STARTplanner
This post may contain affiliate links and we will receive a small commission if you make a purchase after clicking on our link. Read the Disclosure Policy.

There are few things as motivational as amazing planners and best friends working together. When Kristy and Jenny came together to form STARTplanner, they combined both. I admire the way these two women manage to run a company from opposite sides of the country, spend time with both of their families, and take the learning curve of entrepreneurship in stride. You’ll find their enthusiasm for life and work infectious like I do.

Name: Kristy Dickerson and Jenny Grumbling
Location: Headquarters are in Cumming, GA but Jenny is across the country in Portland, Oregon
Title: Co-Founders
Company: STARTplanner
What it is: Daily planners and weekly planners to help you plan goals, projects, finances, and your day to day health and schedule.
Educational Background: Kristy: Business finance degree at Kennesaw State University; Jenny: Graphic design degree

What inspired you to start STARTplanner?

K: It started with an idea for a book, and I reached out to Jenny because she’s a graphic designer. She loved it and shared a dream of hers that she one day wanted to create and design a planner. That’s all it took. Light bulb moment and we haven’t looked back since.

What does a typical day look like for you?

K: I wake up every day at 5 a.m. I’m at the gym by 5:30, I work out, and then I’m back home by 6:30 a.m. Then I shower, get the kids ready, and eat breakfast. My typical workday is from 8 a.m. to 4 p.m. I typically get in the office and organize my morning with lists and Jenny and I Skype at 8:30 a.m. (5:30 a.m. her time). We set goals & intentions and delegate out tasks for the day. As far as every day goes, my tasks are completely different from running and overseeing operations and finance.

J: Organized, of course! But really, I get up and am on Skype by 5:30 a.m. every morning with Kristy, we work together until 1 p.m. (my time), and then I usually work alone for a couple of hours in the afternoon or evening, balancing work with my kiddo, house, dog and…well, life!

If you could have given yourself a piece of knowledge or advice when you started what would that be?

K: I mean can I pick only one?!?! Okay, just one…For me, it is to delegate and get help. I am a doer and sometimes it’s easier and faster to just do it myself. BUT I am learning that by showing, teaching, and guiding, it has transformed and broadened our ability to have an impact.

J: For me it would be knock out the hard stuff first — whether it be an email you are dreading, a project you know will be time consuming, etc. Otherwise it weighs on your mind and adds unneeded stress.

Would you do anything differently?

K: Not a thing. I could list out things we’ve learned about freight and cash flow, etc. But honestly I wouldn’t do anything different. That is what you do, you learn!

J: I agree. We are where we are today because of both our successes AND mistakes!

How do you define success?

K: Very good question and it is something I teach on often. So many people don’t define success and I think it is important, when setting your SMART goals, to define what it is. For me, success is being intentional every day with my actions both inside the office and out; excited for each and every action that I get to choose to make.

J: Being able to live my life in a way where I don’t have to stress out about my family and future — it’s very liberating!

What’s been the hardest part of starting your own business?

K: Cash flow. We started this business while we both had our own businesses and we didn’t want to invest anything…and I had a newborn might I add. So the question was can we bootstrap a startup with investing zero cash and turn a profit fast? We were able to, but cash flow was something that we have really had to learn.

J: Never being able to turn your brain off, taking big big leaps of faith, not always knowing the “right” answer (that’s the scary part!).

What has been the most rewarding part of starting your own business?

K: Jenny might kill me for saying this. I have started other businesses, but probably one of the most rewarding things of THIS business is seeing Jenny excel and being able to live her intended life with STARTplanner being her financial source of income. I know it sounds cheesy but it is true. For me, this company enabling other people to succeed is my biggest reward.

J: Seeing people get excited about the products that we pour our hearts and souls into — and seeing it change people’s lives, and having a business partner who isn’t afraid to push me and help me grow — and vice versa!

How has social media helped shape your brand?

K&J: If you are a company and you say social media has no impact in today’s society, you have missed the boat. It has been instrumental in helping us get the word out about our planners! We live in a world of instant gratification, so for someone to be able to watch our video, learn more, join our Facebook community and see what all the hype is about has been HUGE for us! We use both Kristy’s channel(s) @kristydickerson as well as STARTplanner’s @startplanner.

What are your hobbies? What do you do when you’re not working?

K: I love to work out , travel, and hang with my friends, family, and my boys. And I also love to decorate. I am a self-proclaimed DIYer that doesn’t have time to DIY. Holla!

J: I live in the Pacific northwest, so we do a ton of hiking, go to the beach, camping, etc. I also have a teenage son, so I spend as much time as I can soaking up every minute before he leaves for college!

How do you balance your work with your personal life?

K: Does it always happen? No. But by setting boundaries, being efficient, outsourcing, delegating…I mean this list can go on and on…actually it will. Check out for a little peek of something that I am working on. That’s right, I’m writing a book!

J: I’m a single mom, so sometimes this one gets tricky, but the great thing about working for yourself is that you can work anywhere, so on those days that I do need to work long hours, at least I can work from the couch or kitchen table and hang out with my son.

What’s the one thing you didn’t expect to learn or do when running your own business?

K: Logistics. Do you know how much it costs and how long it takes and how to insure and store over 8,000 pounds of cargo? Yeah, me either.

J: Honestly? About 80% of what I do. I am a designer by trade which is what I expected to do — and I DO, but there’s SO much more planning, forecasting, customer service…the list goes on!

What’s the best piece of business advice you’ve received?

K: Honestly my best advice is not something I have been given I have just seen it. Both of my parents are entrepreneurs and seeing them just work hard. Work is the only way you will get anywhere.

J: Take pride in your work. Don’t take shortcuts and always look for ways to improve.

What about advice for marketing and self-promotion?

K: Be authentic. Be you. No one can duplicate who you are with your unique set of skills. Always stay true to yourself.

J: Find the “voice” of your company and stick to it!

Which of your planners is your favorite and why?

K: I am a Hustle girl. It fits my life and style the best. I have a lot to manage so I need to plan daily. So, it is the one I “hustle” with.

J: I’m a Hustle girl too. My to-do list is always a mile long, so it helps me organize and delegate.

What’s next for you?

Kristy & Jenny– Growth. We know what we have and what is at our core. Striving for perfection and continuing to impact as many people as possible. Oh and that book of course!!!

Real Talk With the Founders of STARTplanner

Last modified on November 7th, 2016

You Might Also Like

Follow us on Instagram @earnspendlive