Today we’d like to introduce you to Jenna Colombo.
Alright, so thank you so much for sharing your story and insight with our readers. To kick things off, can you tell us a bit about how you got started?
I’m just another privileged white girl from the Midwest.
There’s nothing extraordinary about me except that, maybe, you could say I’ve got a little of that Kobe Bryant “Mamba Mentality,” without the basketball.
I wrote and published more than 200 articles for the local newspaper before high school graduation. My school counselor said, “news is dead,” so I built what people now call a “skill stack” across print, web, and video. My unfair advantage was that I found a mentor who was willing to train me hands-on. She held me accountable and forced me to continually improve, get uncomfortable, ask better questions, identify the heart of a story, and turn something complex into something people understand, care about, and act on.
That training and endurance paid off. My first job after college was with a $2 billion endowment, and a year later, because of my subject-matter expertise, I was recruited by a venture capitalist to build the largest privately owned tech incubator in the Southeast. I have partnered with many early-stage companies to build from the ground up, make a pivot, and/or raise strategic capital. My happy place is at the intersection of story, strategy, technology, and growth.
They say that good journalists make their own luck, and I believe it’s because most journalists are unafraid to show up and ask hard questions.
It has been a truly humbling experience to work with dozens of people who are the absolute best at what they do: former editors at The Washington Post and Forbes, Pulitzer Prize-winning journalists, and visionaries bold enough to leave SpaceX and Apple to build their own companies. My clients tend to be inventors and creators introducing hyper-specialized AI-powered technology, new rocket fuel, or safer eVTOL battery systems to the market.
People who pursue excellence tend to attract other people who are pursuing excellence. My friends worked very hard to build something out of nothing, and that’s how we can relate. The women who have been there for me on my hardest days include a Shark Tank Golden Ticket winner and an Olympian. They are both in the continual pursuit of excellence, and they’ve made seemingly impossible things possible within their own spheres of influence.
The twist here is that I thought I had become the kind of person I was supposed to become. I’m embarrassed to say I was deeply disappointed and unsatisfied in my 20s. It took several hard lessons to discover—finally, now that my hair is turning gray and I’m celebrating 10 years in business—what I believe may be the key to success: coachability.
To be more accurate, when we’re coachable we’re leading with the purpose of listening, learning, and we’re open to the possibility that we may need to adapt.
The most fascinating part of my work has been evaluating what actually happens when someone succeeds or fails. It can be counterintuitive. The founder that dumps the most money into sales and marketing is not necessarily the one most likely to succeed. The company retaining its best people long-term is not necessarily the one paying the highest salaries. More often, it’s the founder who operates with genuine humility, relentlessly questions their own assumptions, and builds a culture where people are encouraged to fail fast, learn, and iterate.
When we can demonstrate those behaviors with evidence, we essentially have the key ingredients investors are looking for when deciding whether to provide capital. But positioning yourself for success requires a founder to become very comfortable with discomfort. Most people aren’t. And that, in part, is why enduring success stories are so rare—they’re less like overnight shooting stars and more like the result of repeatedly making difficult decisions long after the excitement has worn off.
I’ve experienced that personally, and I’ve witnessed it enough times firsthand to know better, advise better, and course-correct faster—and, hopefully, with a little more grace.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
The hardest challenge for me has been my own value system.
If I wasn’t at work in my 20s, I was probably alone at a cigar bar ordering extra-dirty martinis, like Carrie from Sex and the City if she were a curvy brunette tech nerd walking the streets of Melbourne, Florida.
I had achieved what I believed was the American Dream. I was working for myself on a beach and making six figures. I didn’t have words for it at the time. It was like an incongruent gut feeling. I had a sense that “the jig is up”. Worse, I was beginning to realize that I could no longer reconcile my hardworking, all-in entrepreneurial self with the quiet voice in the back of my mind that desperately wanted the thing I had publicly (many times) rejected: a partner and a family.
It’s a harsh reality when, if you’re anything like me, you look in the mirror one day and realize the lies you believe about yourself are masquerading as confidence and competence.
In my situation, I had no choice but to change my value system. Choosing the truth over the lie was laced with heavy, long-lasting consequences for me, including legal and financial hardship, the loss of many friendships, my waterfront home, and essentially everything I worshipped.
Appreciate you sharing that. What should we know about Jesus In Your Business?
**What would change if Jesus actually shaped the way you do business?**
Jesus In Your Business is a community for Christian founders and leaders who want to follow Jesus into the way they lead, make decisions, build companies, and serve people. Our core focus is The Word.
We share the testimonies that shape both our character and our companies with a focus on **Faith. Humility. Coachability. Character. Purpose. Leadership. Stewardship.**
**Join the Jesus In Your Business community:**
https://substack.com/@jesusinyourbusiness
**Pre-order Jenna’s book, *Jesus in Your Business*:**
https://a.co/d/05lo0tYn
Annual Strategic Retreat: Available to any business anywhere, we host an upbeat two-day strategy and video production day that begins with listening and aligning teams around a clear go-to-market strategy. We then film 365 days of content designed to nurture the strategic vision. The result is 365 days of B2B outreach and scheduled social media to support sales and marketing teams. More at reelgoodnews.com
We’d love to hear about how you think about risk taking?
We all mature in different ways and for different reasons. The greatest challenge or obstacle I have experienced also required me to be reborn.
By surrendering everything, I received the greatest treasure: the revelation that victory and success in business and life belongs to Jesus Christ.
Once I chose Jesus and was baptized, I was surprised that He did what He said He would do. It was the difference between seeing in black and white vs seeing in color and completely starting over (2 Corinthians 5:17). Even my mundane everyday experience has been made incredibly rich by reading the Bible, which is alive with the living words of the One who is and was and is to come. I know now that it was Jesus who rescued me in an effort to reconcile me back to Himself (this is what He does repeatedly in the Bible) so that I might choose to live for Him and type these words today.
In the past, I thought Christianity was sort of like a Hallmark card that you receive from your second cousin twice removed. Cute but unrelatable and irrelevant.
There must be a reason, afterall, that most of us are in a perpetual state of numbness and in need of distraction. Obviously, we do find ourselves more “connected” and simultaneously more disconnected. It says something about us that the most loving moment of our day may be a hot Starbucks cup with our name on it, filling us with false hope when we desperately desire to be known and loved. I do believe many of us suspect deep down, “the jig is up.” It is being revealed to the most unlikely people of all (you and me) that only God has the capacity to fill us, the true King of Kings and Lord of Lords. The God who is and was and is to come.
“Don’t be deceived, my dear brothers and sisters. Every good and perfect gift is from above, coming down from the Father of the heavenly lights, who does not change like shifting shadows.”
— James 1:16–17 (NIV)
This was the Scripture in the Bible that unlocked a new level of freedom for me. Unfortunately, I had to lose everything to surrender control. My prayer is that the next generation of believers won’t need to hit rock bottom to fully surrender their pride.
And with that, I encourage you to go to a church near you and find what works for you. At a minimum, go find a Bible. If you’re curious, you’re welcome to pre-order my book Jesus In Your Business or sign up for our next virtual workshop. Our team will relentlessly explore what it means to be coachable and pursue faithfulness in life and business by putting Jesus at the center of it all. I know better than to believe this business is my own. Proceeds will help fund no-strings-attached microgrants to founders, leaders, and builders in underserved communities. If you’re building better communities and could use some help getting off the ground, you can apply for our first batch of grants today at www.jesusinyourbusiness.com.
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