A Day In the Life of ChipMonk's Co-Founder & CEO

by David Downing (ChipMonk CEO)

Before co-founding ChipMonk in 2019, I spent years working for more “conventional” companies (Contract compliance at KPMG, Management consulting at Alvarez & Marsal, Audit and financial planning at Southwest Airlines to name a few). Over time, an entrepreneurial “itch” started to grow within me, and I found myself always wondering what life as a startup founder was actually like. Well, here’s a post for past me and hopefully for some of you future founders out there – a day in the life of a specialty food startup founder.

ChipMonk has been in business for a little over 2 years at the time of me writing this, so my day-to-day is pretty drastically different from what it was even 6 months ago. My co-founder Jose and I have been fortunate to have grown enough to be able to build out a team of awesome people to help us with all the daily tasks involved in running the business (production, fulfillment, customer service, marketing, sales, etc.). When we started, we did literally everything ourselves, but as we work to build a business that extends beyond ourselves, our responsibilities and daily activities have shifted. If you ever want to learn more about life in the very earliest days, check out some of our earlier blog posts or simply shoot me a message on LinkedIn (here’s my profile).

5:30 AM – My alarm goes off and I fight an internal battle on whether to get up or not. This is made 1,000X more difficult when you have an amazing partner or spouse still slumbering away and all you want to do is stay cozy with them. On my good days, I force myself up, brush my teeth, get dressed, chug a glass of water, make a k-cup coffee to go (sweetened with tasty monk fruit drops), and drive off to the gym. I do my best to not check my phone or email at this time. Usually I end up looking though (it’s an addiction), and 90% of the time when I do it throws me into a horrible mindset because all I can do for the rest of the morning is think about whatever issue or question came through.

6:00 to 7:00 AM – If I managed to get up in the step above, I head to the gym and do an hour workout usually mixing some cardio and weight training. It really helps to have a set routine (e.g., 3-5 different workouts that you do each week for a set number of weeks) and ideally some goals here whether it’s to lose some weight or achieve personal records with strength/cardio movements. I love how exercising forces me to push the clutter out of my mind. I can’t think about an email or issue because I’m focused on not dropping a weight on my head or collapsing from being tired. This clears my mind and the endorphins put me in a positive mood coming into the day.

7:00 to 9:00 AM – I’d love to say I pre-write a list of top priorities for each day but honestly, I don’t. I really should, but most of my days start with a kind of panicked rush to pack all our online orders from the day prior. Jose and I used to do this all alone but now we have two awesome team members who take lead on fulfillment. Usually we pack ~30-50 e-commerce orders per day (from our website, Amazon, Walmart.com) plus a few larger packages for wholesale (some of these come direct, some from our broker, and others from online wholesale platforms like Faire and Abound). We allow a lot of customization for online orders and we write a hand-written custom note for every single order, so this process is pretty time consuming. 

Around this time, I also check in with our head of operations Nathan to see what the baking team is working on for the day and to discuss any immediate issues or testing we want to do for the day. Nathan will often make single small test batches of things like new flavors, new products, or small tweaks to existing products to see if we can make them better. Our baking team also has a weekly meeting every Tuesday morning that I’ll sometimes join to share any big announcements as well as praise for any team members going above and beyond. We use those meetings to track our overall production efficiency as well – if the team hits certain efficiency goals, they all get a monthly bonus.

9:00 to 11:00 AM – Depending on the day of the week, this time is typically filled with either team meetings or one-on-ones between me and the team mates I work directly with.

We have a weekly leadership team meeting with me, my co-founder Jose, our operations lead Nathan, and our digital marketing lead Michael. We have a metrics scorecard that we review each week (it has things like daily sales, working capital, production output and efficiency) as well as a list of action items for the week assigned to each of us. We also have a weekly marketing meeting with our content and social media folks (the same ones who pack the orders in the morning!) where we talk through our marketing calendar for the coming weeks as well as any initiative relating to content and paid digital advertising.

I also try to have bi-weekly one-on-ones with everyone on the team. Each month, I have everyone set goals, and we use those goals to frame our chats. Generally, I ask for any feedback on what I can do better for them and how they’re feeling about their role. While these meetings take time, it’s important that everyone feels heard and so I can collect feedback and ideas to help improve the team and company. I picked up this practice from my time at Southwest Airlines and highly recommend it to anyone whether you are a leader of others or you want to improve your relationship with your own leader. I do my best to have these meetings off-site (Starbucks typically) so we can get away from the chaos of the warehouse/kitchen and have a clear-minded conversation.

11:00 AM to 5:00 PM – I’ll normally eat a quick lunch at my desk. Usually, I meal prep with my wife or buy prepared meals from My Fit Foods so I can track calories (I like to use MyFitnessPal) and save some money. I always have a sweet tooth after lunch, but luckily, I can just grab a cookie since we bake thousands of them :)

Afternoons are usually a mixed bag but can offer larger blocks of time for more focused work. Here are things I’m typically doing:

Sometimes Jose and I may have to jump over to the bakery side in the afternoon to help package up our cookies as well. Our team is pretty small so if someone is out sick or on vacation, they’ll usually need a helping hand!

UPS typically swings by our warehouse at 4:30 PM to pickup our larger packages for the day, and I normally use that as my cue to head home. Believe it or not, my days aren’t too long!

5:00 PM Onwards – Once I get home, I rarely do any work. I try to shut off my brain from that part of the day and focus more on recharging and spending time with my wife. I almost immediately hop on the couch for a snack (I love Schoolyard Snacks keto puffs, IWON Organics protein puffs, and HiLo tortilla chips) plus some streaming TV (I’m a big fan of anime, anything with Chef Gordon Ramsay, and lately trashy island-themed reality shows like F Boy Island and Too Hot to Handle). 

Once it cools down in the early evening, I like to go for a walk outside with my wife where we can talk to each other about our days and start planning for the weekend and future vacations. Dinners are typically another prepped meal popped into the microwave.

Normally I’ll end the evening with a boozy beverage of sorts (bourbon + diet ginger ale is a favorite) and try to be in bed around 9:00 PM. I’ll read for a little bit (either something trashy and fun like Warhammer 40K or something focused on personal or business improvement like How to Win Friends and Influence People). The key to being able to get up early in the morning is to go to bed early so I try not to stay up too late. I also try to keep my phone as physically far away from me as possible when I get into bed to prevent me from going down a TikTok / LinkedIn / Instagram scrolling binge which always ruins my chances of sleeping well. I actually charge my phone on the floor several feet away from the bed so I can’t instinctively grab it.

Weekends – Weekends for me are a chance to recharge some and spend time with my wife and friends. Usually on Saturdays my wife and I will grab a coffee to go and head to a local park for a walk. We’ll try to do some meal prep cooking too and then in the evenings maybe go out somewhere nice for dinner or just stay at home and eat something we shouldn’t (Edwards Key Lime Pie, HEB Red Velvet Cake, Costco Kirkland Champagne are things I dream of haha). On Sunday, I’ll often come into the office to catch up on some work or will do so for a couple of hours at home. I just like to clean up my inbox so I’m not overwhelmed Monday morning.

Probably about once every two months we’ll try to do a weekend trip as well. With Covid, we did a lot of road trips to nearby small towns and stayed at fun Airbnb’s. Lately we’ve been able to fly some more and visit family in Chicago or Nashville. Later this year we’ve got plans for Albuquerque, Africa (Tanzania!), and Orlando (Star Wars Galaxy Edge here I come!).

Some of you may be surprised that my life isn’t constant “grinding”. I don’t work 12+ hours a day every day and I actually have time for things like weekend trips and sleeping in on weekends. This was not always the case. The only reason I can do those things is because Jose and I focused on building a business beyond ourselves. This concept is covered in great detail in a good book called The E-Myth Revisited: Why Most Small Businesses Don't Work and What to Do About It. I highly recommend any startup founder think in this way from the get-go. If you end up having to do 100% of all the things yourself for your business, you will absolutely burn out. You have to find awesome team members and build processes so the business can run without you.

With that said, the stress of owning and running a business never leaves you, and, at the end of the day, your still 100% responsible for anything that could go wrong. I’ve had many evenings and weekends ruined by anxiety over issues with the business. This type of stuff can lead to pretty long spells of depression. One thing that helped me with this came from a conversation with my mom. I was complaining about how overwhelmed I felt and how frustrated I was with some issues at ChipMonk and she reminded me that when I was working corporate jobs, I complained all the time too. I think at the end of the day anxiety is going to come from anything you do (assuming you care about what you do), but personally I’m more satisfied knowing that it comes from something I’m actively trying to build than something owned by another. It’s also incredibly important to have a network of supportive friends and family along the way, and to invest time in those people. At the end of the day, they care about you as a person, not you as your business. To maintain my sanity, it’s important to remember the difference.

On that happy note, I hope this shed some light on life as an entrepreneur! If you ever want to talk about your own journey or feel like I could help in any way, connect with me on LinkedIn and shoot me a message: here’s my profile. 

Thanks for dropping by the ChipMonk Blog! While your here, be sure to check out ChipMonk Baking’s HUGE variety of soft-baked keto cookies, baking mixes, and sweeteners. And don’t forget to subscribe to our newsletter for the latest recipes, deals, and updates from the ChipMonks. You can also join our Text VIP program by texting CHIPMONK to (833) 645-0998