Authentic &


Matt Douglas, Founder and CEO of

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Every Entrepreneur Needs a Rock

Let me take you back to the spring of 2015. Most evenings and weekends I would spend in my office at home, working hard on an idea that I didn’t know how to define and wasn’t able to explain. I spent a lot of time in the office doing research online and staring at Powerpoint slides that I tried to create to explain the idea. At some point, my wife Jessica would call me down out of my hole to make sure I had something to eat, and make sure I was keeping sane. She was my rock.

Lots has been written about why you should have a co-founder when you start a company, but I haven’t come across too much that talks about how important it is to have a rock in your entrepreneur life. I would argue that a rock is just as important as a co-founder. Do you have someone in your life that is your entrepreneurial rock? Maybe it’s your spouse — but it might be a close friend, a mentor, or even your parent. How do you know if you’ve found your rock? Here’s a list of just a few of the things that Jessica does for me to help me succeed everyday.

She’s non-judgmental: I’ve never met someone as non-judgmental as Jessica (really, ask anyone who has ever met her). Even in the early days of Punchbowl, when my ideas were unformed and unintelligible, Jess never passed judgement. Instead she nodded in agreement, asked simple questions, and never once criticized my ideas. More than anything, your rock should understand that you need positive reinforcement, especially in the early days of your start-up venture.

She’s outside my bubble: Jessica and I joke that we could never work with each other, even though I’m sure we could. However, I don’t want to. She keeps things real for me by not being in my bubble. I know I can count on her to get an outsiders view of what I’m working on because she doesn’t live and breathe in the technology or start-up world. Get someone out of your bubble to be your rock and you’ll always have your feet on the ground.

She listens really well: The first night I met Jess in college, I was taken with how she listened to me. Years later, she exhibits the same behavior day after day, night after night. She’s always there to hear about what happened that day, listen to me talk about my frustrations, and look at me with those caring eyes that tell me everything is going to be ok. Most entrepreneurs have opinions, and lots to say. Make sure you have someone in your life who really is willing to listen.

She cares for my well-being: Like most entrepreneurs, when I get focused (or I’m stressed) I tend not to take care of myself. Without Jess in my life, I probably wouldn’t have eaten many nights or even stepped away from my computer. Find someone in your life who cares about your well-being and be thankful and appreciative when she makes you take a break to eat dinner.

She can be my harshest critic (when asked): Most of the time, Jess is my supportive rock. But everyone once in a while, she’ll keep it real by providing harsh feedback when I ask for her opinion. A few months ago, I asked her what she thought of a marketing campaign that we were doing, and she didn’t mince words: “Yeah, what the hell was that?” she said. Her point was made, and I heard it loud and clear.

She takes care of things in my life: Here’s a quick test to see if you have a rock in your life. Let’s say you have an unexpected meeting in the morning, and all of your good shirts are in the laundry. You need to get a shirt cleaned and ironed in a hurry. Who do you call? What if you need to get a package mailed before noon? Who will go to the post office for you? I can’t tell you the countless times that Jess has stepped in and took care of simple but important things in my life. I’m forever grateful for everything she does to take care of things in our family’s life.

She loves me, unconditionally: Let’s face it — despite what everyone may think from the outside, some days as an entrepreneur/CEO just really suck. It’s takes a certain type of disposition to be able to withstand a constant barrage of people telling you “no” and somedays it’s just too much to bear. And on those bad days, you might act like an irrational jerk and you may even take out your anxieties and frustrations on the one who loves you the most. And yet, despite all of this… she loves you, unconditionally and she reminds you just how much. She wants you to succeed so that you feel fulfilled in your career and she is happy to come along on your journey. When you find this person, hold her close. It’s like finding the end of the rainbow.

As I wrote this post, it’s been great to reflect on how important Jessica is to the success I’ve had as an entrepreneur and CEO. Simply put, I wouldn’t be where I am today without her steady hand and guidance. Jess: you are my rock.

Happy 8th Anniversary, love.

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©2020 Matt Douglas