Intro: It’s not every day you have a chance to interview someone who was a successful start-up founder and, initially in her words, “a stay-at-home mom” who was bored. She went on to discover a product category where her domain expertise was limited, led a minority equity round with a private equity firm(K1), took on a majority equity partner (Vista Equity Partners), and later guided the exit to a strategic buyer in 2023. Well, Monica Enand did just that, all while growing the company she founded, Zapproved, to approximately 170 employees, earning recognition more than once as one of the top 100 companies to work for in Oregon, and leading the company as CEO over a sixteen-year time horizon.

Having met Monica over 15 years ago when she was running Zapproved in its early days from a small office in Portland, OR, I was excited that she was inclined to share her story on the Bending Rules Pod. Since I was already impressed with Monica’s journey from afar, it was yet another lesson in perseverance, grit, and belief in oneself. I was also reminded that most entrepreneurs, regardless of how overtly successful they have become, have experienced their dark or difficult hours, and Monica’s journey was no exception.

We talked for an hour, but I could have easily spent a day with her unpacking the details of her journey. Hope you enjoy! ~Onward

As a reminder, I am terrible at marketing, but if you like what you hear and are learning please follow and share the pod.  I am now also making content available on a youtube channel (Bending Rules) where “shorts” will be shared to codify some of the instructive remarks of pod guest, if one is not inclined to listen to a whole episode😊.  Let's help as many entrepreneurs as possible, also, my advertisers will appreciate it. Wait a minute, what advertisers? :)

2:16 -- Zapproved Journey and Origins of entrepreneurism

12:53 -- No domain experience, finding a product niche

14:12 -- Get out the credit card, early days of financing

22:59 -- Moment of Truth. Am I going to have to shut this down? Where she found support

26:14 -- Raising capital in tough market (no financing for 5 years)

30:01 -- Wait a second now investors like us? Navigating PE relationships and deciding on a partner

40:07 -- Getting knocked down and journey to build a world class culture

48:40 -- Importance of networking your entire journey

55:25 -- Overcoming gender bias

59:12 -- Everyone needs to get lucky along the way, Monica shares one story

1:04 -- Parting advice for entrepreneurs

Thanks again Monica for being an awesome guest!

Stay tuned, more entrepreneurs and rule breakers to follow....