In this episode of the How I Started Career Stories podcast, I sat down with Andrew Kappel to share the story behind launching Outworks—a content agency helping founders and executives consistently show up on LinkedIn.

I talked about how I made the leap from a 15-year sales career into entrepreneurship, what it was like juggling two calendars while secretly building a company on the side, and the real tipping point that pushed me to go all in. Spoiler: it involved a terrible acquisition and one unforgettable LinkedIn post that read: “There’s never a perfect time to start—start anyway.”

Outworks didn’t start out as what it is today. We originally launched as a cold email agency—but quickly realized that wasn’t the work we wanted to do. We pivoted hard into helping executives create done-for-you content on LinkedIn, and we haven’t looked back.

Now, we work with CEOs and teams who want to build trust, visibility, and a real voice in their industry—but don’t have the time or bandwidth to do it alone. I also share how we’re helping companies create cultures of content creators and why that might be the best competitive edge going into 2025.

Takeaways

• I spent over a decade in sales before co-founding Outworks.

• I secretly built the company while still working full-time—managing two calendars and moonlighting on prospect calls.

• A bad acquisition experience pushed me to finally bet on myself.

• We started with cold outbound but quickly shifted to high-quality LinkedIn content.

• The demand was clear: founders wanted to post consistently but had no time or strategy.

• There’s no easy button for content—consistency always wins.

Today, we help CEOs and executives grow their brand and drive demand through invisible marketing.

More companies are asking us to build entire ecosystems of internal creators—not just help the CEO.

If you’re not visible on LinkedIn, you’re falling behind. The next generation of buyers expects it.

Chapters

00:00 – Intro: Meet Jared Gibson of Outworks

01:37 – My Sales Career & How I Got the Startup Bug

05:21 – How a Bad Acquisition Pushed Me to Start

07:54 – Moonlighting with Two Calendars

08:44 – Our Original Business Model (and Why It Failed)

11:06 – The Pivot to LinkedIn Content

13:22 – What Our Clients Actually Wanted

15:28 – Why Most People Quit Posting Too Soon

17:03 – The Power of Invisible, Organic Marketing

19:55 – Why CEOs Need to Be on LinkedIn in 2025

21:45 – Helping Teams Become Content Creators

22:28 – What I’m Excited About Next

Outworks – Content for Founders & Executives:

https://www.outworks.io

My LinkedIn Profile

https://www.linkedin.com/in/jaredoutworks

My Podcast

https://open.spotify.com/show/1Xv7C9WFxZHeoARrm8EDc5

Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: ⁠https://www.linkedin.com/in/andrewkappel/