Podcast thumbnail for How I Started - Career Stories Podcast

How I Started - Career Stories Podcast

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by Andrew Kappel

5.0(1 reviews)
12 episodes
Updated Daily
Accepts GuestsHas SponsorsLocation 🇺🇸
37

Podcast Authority

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PoorBased on show quality, social media presence, reviews, charts, and more
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Quality73
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Podcast Overview

Tune in to hear how CEOs, Entrepreneurs, and Executives got started on their career journey.

Language

🇺🇲

Publishing Since

2/18/2025

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37

Podcast Authority

Beta
PoorBased on show quality, social media presence, reviews, charts, and more
Pod Engine
Quality73
Social0
YouTube0
Engagement0
7
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2
Good Performance
10
Growth Opportunities
excellent
Episode Length
34 minutes
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good
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Every 12 days

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Recent Episodes

Episode thumbnail for Ep. 12: Todd Caponi - Journey from Sales Leader to Author, Speaker, and Sales Historian

July 11, 2025

Ep. 12: Todd Caponi - Journey from Sales Leader to Author, Speaker, and Sales Historian

Host Andrew Kappel interviews Todd Caponi, author and founder, about his journey from sales leader to author, revealing how transparency in sales builds trust and improves conversion rates in this interview.

Episode thumbnail for Ep. 11: David Politis, Entrepreneur, Founder, and Creator: Not Another CEO | How I Started

June 13, 2025

Ep. 11: David Politis, Entrepreneur, Founder, and Creator: Not Another CEO | How I Started

Host Andrew Kappel interviews David Politis, a serial entrepreneur, who recounts his journey building and scaling companies like BetterCloud, emphasizing customer focus and transparent leadership, which offers insights into entrepreneurial success.

Episode thumbnail for Ep.10: Jared Gibson, Co-Founder Outworks - Path to Entrepreneurship and the LinkedIn Journey

May 2, 2025

Ep.10: Jared Gibson, Co-Founder Outworks - Path to Entrepreneurship and the LinkedIn Journey

<p>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.</p><p>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.”</p><p>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.</p><p>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.</p><p><br /></p><p><strong>Takeaways</strong></p><ul><li>I spent over a decade in sales before co-founding Outworks.</li></ul><ul><li>I secretly built the company while still working full-time—managing two calendars and moonlighting on prospect calls.</li></ul><ul><li>A bad acquisition experience pushed me to finally bet on myself.</li></ul><ul><li>We started with cold outbound but quickly shifted to high-quality LinkedIn content.</li></ul><ul><li>The demand was clear: founders wanted to post consistently but had no time or strategy.</li></ul><ul><li>There’s no easy button for content—consistency always wins.</li></ul><p><br /></p><p>Today, we help CEOs and executives grow their brand and drive demand through invisible marketing.</p><p>More companies are asking us to build entire ecosystems of internal creators—not just help the CEO.</p><p>If you’re not visible on LinkedIn, you’re falling behind. The next generation of buyers expects it.</p><p><br /></p><p><strong>Chapters</strong></p><p>00:00 – Intro: Meet Jared Gibson of Outworks</p><p>01:37 – My Sales Career &amp; How I Got the Startup Bug</p><p>05:21 – How a Bad Acquisition Pushed Me to Start</p><p>07:54 – Moonlighting with Two Calendars</p><p>08:44 – Our Original Business Model (and Why It Failed)</p><p>11:06 – The Pivot to LinkedIn Content</p><p>13:22 – What Our Clients Actually Wanted</p><p>15:28 – Why Most People Quit Posting Too Soon</p><p>17:03 – The Power of Invisible, Organic Marketing</p><p>19:55 – Why CEOs Need to Be on LinkedIn in 2025</p><p>21:45 – Helping Teams Become Content Creators</p><p>22:28 – What I’m Excited About Next</p><p><br /></p><p><strong>Outworks – Content for Founders &amp; Executives:</strong></p><p><a href="https://www.outworks.io" target="_blank" rel="ugc noopener noreferrer">https://www.outworks.io</a></p><p><strong>My LinkedIn Profile</strong></p><p><a href="https://www.linkedin.com/in/jaredoutworks" target="_blank" rel="ugc noopener noreferrer">https://www.linkedin.com/in/jaredoutworks</a></p><p><strong>My Podcast</strong></p><p><a href="https://open.spotify.com/show/1Xv7C9WFxZHeoARrm8EDc5" target="_blank" rel="ugc noopener noreferrer">https://open.spotify.com/show/1Xv7C9WFxZHeoARrm8EDc5</a></p><p><strong>Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn:</strong> ⁠<a href="https://www.linkedin.com/in/andrewkappel/" target="_blank" rel="ugc noopener noreferrer">https://www.linkedin.com/in/andrewkappel/</a></p>

12 total episodes available

Recent guests on How I Started - Career Stories Podcast

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Todd Caponi

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David Politis

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What is How I Started - Career Stories Podcast?

Tune in to hear how CEOs, Entrepreneurs, and Executives got started on their career journey.

How often does this podcast release new episodes?

This podcast updates daily.

Where can I listen to this podcast?

This podcast is available on 4 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

Does this podcast accept guests?

Yes, this podcast regularly features guests.

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