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

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

In this episode of How I Started, host Andrew Kappel interviews Todd Caponi, author of The Transparency Sale and founder of Sales Melon, a sales training and keynote business built around behavioral science and honesty in selling. Todd shares his unorthodox journey—from tech sales rep to SVP of Sales, to CRO of Chicago’s fastest-growing tech company, and eventually quitting to write a book after a surprising buyer behavior study changed his worldview. He explains how embracing transparency in sales not only feels better but actually improves conversion rates. Todd also dives into his rollercoaster entrepreneurial experience, why he says “no” often, how he builds self-discipline using quarterly board-style reports, and what inspired his passion project—the Sales History Museum. Takeaways: - A Northwestern University study on reviews convinced Todd that honesty converts better than perfection. - Revealing flaws in your product or service up front can build trust and speed up decision-making. - After resigning from a high-growth CRO role, Todd had to say no to “can’t-miss” opportunities to stay focused on writing his first book. - Building a business meant experimenting with consulting, training, and keynotes, and then doubling down on what worked best. - The entrepreneurial journey is bumpy, with highs and lows—Todd shares how Q1 2024 was his best quarter ever, followed by a slow Q2. - He conducts solo quarterly reviews (like board meetings) to analyze revenue, buyer demographics, win rates, and business health. - Learning to qualify leads better saved him time and improved his sales process. - Todd's new book,Four Levers Negotiating, aims to replace outdated haggling with a cards face-up, trust-based approach. - The Sales History Museum is a passion project highlighting lost wisdom from 19th- and 20th-century sales books and artifacts. - His mission: Make sales a trusted, admired profession again. Chapters: 00:00– Intro & Sales History Museum Welcome 00:57– From Tech Sales Rep to Leadership & Sales Trainer 03:28– Buyer Behavior Study That Changed Everything 06:10– Quitting the CRO Role to Write *The Transparency Sale* 08:21– Saying No: How Mentorship Helped Todd Focus 10:31– Turning Down Salesforce & Finding the Real Lesson 12:35– Building the Business: Experiments, Focus, and Lessons 15:02– Riding the Revenue Rollercoaster as an Entrepreneur 16:51– Doing Board-Style Reviews to Self-Audit the Business 20:02– Qualifying Leads & Understanding Buyer Roles 22:09– Writing *Four Levers Negotiating* & What It Teaches 26:10– What Is the Sales History Museum? 28:38– Hunting Vintage Sales Books & Artifacts 30:10– Closing Thoughts & Where to Connect with Todd: Caponi:https://www.linkedin.com/in/toddcaponi/https://www.transparencysale.com/Sales History Podcast:https://podcasts.apple.com/us/podcast/the-sales-history-podcast/id1607151709

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

In this engaging episode, host Andrew Kappel chats with David Politis, a serial entrepreneur and multi-time founder. David shares his journey from growing up around his entrepreneurial father to founding and scaling companies, including his experiences with Not Another CEO and BetterCloud. Key Highlights: - Starting Out: David's early exposure to entrepreneurship and his first CEO role at age 23. - Building Not Another CEO: How he is learning from CEOs at scale via podcasts with dozens of company leaders and a community of CEOs sharing real insights and support. - Lessons Learned: The importance of operating rhythm and staying laser-focused on the ideal customer profile (ICP) for successful scaling. - BetterCloud’s Success Story: From door-to-door research to scaling a $70M ARR SaaS business by prioritizing customers and transparent leadership. - Practical Takeaways: The power of consistent, high-value curated content (like a 7-year daily newsletter!) - Building trust by actively involving customers and employees. - Balancing data-driven decisions with customer empathy and product-led insights. Where to Learn More: - Not Another CEO Podcast & Community: https://podcast.notanotherceo.com/ - Not Another CEO Substack: https://notanotherceo.substack.com/ - LinkedIn: https://www.linkedin.com/in/davidpolitis/ - YouTube Channel: https://www.youtube.com/@NotAnotherCEO - Learn more about LeaderLev Pipeline Velocity Consulting:[www.LeaderLev.com](http://www.leaderlev.com/) - Link to Connect with Host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/ Enjoyed the episode? Subscribe on your favorite podcast app. Share this episode with a friend, colleague, or anyone who’d be inspired by David’s story.

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

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 [https://www.outworks.io] My LinkedIn Profile https://www.linkedin.com/in/jaredoutworks [https://www.linkedin.com/in/jaredoutworks] My Podcast https://open.spotify.com/show/1Xv7C9WFxZHeoARrm8EDc5 [https://open.spotify.com/show/1Xv7C9WFxZHeoARrm8EDc5] Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: ⁠https://www.linkedin.com/in/andrewkappel/ [https://www.linkedin.com/in/andrewkappel/]

Ep. 9: Ryan Allis, Serial Entrepreneur and Co-Founder of iContact ($169M) Exit

In this episode of the How I Started Career Stories podcast, Ryan Allis shares how he co-founded iContact at 18, scaled it to over $50 million in annual revenue, and exited for $170 million—all before turning 30. He dives into the scrappy tactics that helped him land the first 1,000 customers, how understanding customer lifetime value fueled growth, and why he chose to walk away from corporate life to build community-first ventures. Ryan also discusses his current work with SaaSRise and GrowthRise—digital-first communities supporting SaaS founders and B2B growth leaders—and reflects on what it really takes to build and scale a purpose-driven business. Takeaways - Ryan started designing websites in middle school and launched iContact as a college freshman. - Early growth came from door-to-door efforts, creative promos, and direct customer contact. - A key early hack: auto-replies to Microsoft List Builder subscribers that drove rapid signups. - Ryan focused on metrics—spending $500 to earn $1,700 in customer lifetime value. - He scaled the company to 70,000 customers and a 60-person sales team before the exit. - iContact was sold for $170M in a full cash deal in 2012. - After the exit, Ryan attended HBS and later launched SaaSRise and GrowthRise. - SaaSRise supports SaaS CEOs with $1M–$100M in ARR; GrowthRise supports B2B sales leaders. - Ryan’s advice: do things that don’t scale at the start, and build something unique that shows your value. Chapters 00:00 - Introduction to Ryan Allis and iContact 01:51 - From Web Design to Email Marketing Startup 07:29 - Early Growth Tactics and First Customers 08:28 - Growth Hacking Microsoft List Builder 10:11 - Understanding Unit Economics and Scaling 11:52 - Preparing for Exit and Acquisition 14:02 - Life After the $170M Exit 17:23 - Building SaaSRise and GrowthRise 25:07 - Managing Fast Growth and Community Building 27:30 - Lessons for Aspiring Founders 29:31 - Book Recommendations and Legacy Keywords Ryan Allis, iContact, SaaSRise, GrowthRise, SaaS growth, startup journey, founder story, email marketing, business exit, bootstrapping, venture capital, startup tips, SaaS founder community, entrepreneurship Resources & Links SaaSRise – Digital community for SaaS founders: https://www.saasrise.com/ [https://www.saasrise.com/] GrowthRise – Community for B2B sales & marketing leaders: https://www.growthrise.com/ [https://www.growthrise.com/] Ryan’s LinkedIn: https://www.linkedin.com/in/ryanallis [https://www.linkedin.com/in/ryanallis] Books by Ryan AllisMagic Year: How to Design a Life You Love – [Buy on Amazon] (https://www.amazon.com/Magic-Year-Design-Life-Love-ebook/dp/B0CCK5C4W1?ref_=ast_author_dp [https://www.amazon.com/Magic-Year-Design-Life-Love-ebook/dp/B0CCK5C4W1?ref_=ast_author_dp]) Zero to One Million: How I Built A Company to $1 Million in Sales . . . and How You Can, Too – [Buy on Amazon](https://www.amazon.com/Zero-One-Million-Built-Company/dp/0071496661 [https://www.amazon.com/Zero-One-Million-Built-Company/dp/0071496661]) Contact Ryan: ryan@saasrise.com Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/ [https://www.linkedin.com/in/andrewkappel/]

Ep. 8: Alec Sharp | a 4+ Decade Independent Consulting Journey

In this episode of the How I Started Career Stories podcast, Alec Sharp shares his extensive journey as an independent consultant over the past 4+ Decades. He discusses his early career experiences, the transition to independent consulting, and the innovative approaches he developed in data modeling. Alec emphasizes the importance of focusing on the people who do the work and how his business model revolves around consulting, developing intellectual property, and delivering value through teaching. He reflects on the evolution of data modeling needs and concludes with insights on maintaining a successful independent consulting practice. Takeaways - Alec Sharp has 4+ Decades of experience as an independent consultant. - Early career lessons include the importance of taking initiative and not being constrained by job titles. - Transitioning to independent consulting doubled Alec's income overnight. - Building a unique value proposition is crucial for success in consulting. - Alec emphasizes the importance of focusing on the people who do the work. - His business model includes consulting, developing IP, and teaching. - Alec decided against building a larger firm after realizing he enjoys hands-on work. - Data modeling needs have evolved, but the fundamentals remain important. - Alec's approach is to give away knowledge, leading to more opportunities. - Contacting Alec directly is encouraged for those interested in his work. Chapters 01:07 - Early Career and Lessons Learned 07:53 - Transition to Independent Consulting 10:45 - Innovating in Data Modeling 12:42 - Client Acquisition and Engagement 14:34 - Focus on the People Who Do the Work 16:40 - The Business Model of Consulting 18:27 - Deciding Against Building a Larger Firm 24:25 - The Evolution of Data Modeling Needs 27:56 - Conclusion and Resources Learn more about Clariteq Systems Consulting: https://www.clariteq.com/ [ https://www.clariteq.com/] Read Alec’s book Workflow Modeling:Workflow Modeling: Tools for Process Improvement and Application Development, 2nd Edition [https://www.amazon.com/Workflow-Modeling-Application-Development-Second/dp/1596931922] Connect with Alec Sharp: https://www.linkedin.com/in/alecsharp/ [https://www.linkedin.com/in/alecsharp/] LucidChart Webisodes series on process mapping methodology: https://youtube.com/playlist?list=PLUr2vo1BNYKWYrzCjCXmYXimCOFTWDTaB&si=tauHVuIhC4VSXNSs [https://youtube.com/playlist?list=PLUr2vo1BNYKWYrzCjCXmYXimCOFTWDTaB&si=tauHVuIhC4VSXNSs] Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: ⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/andrewkappel/ [https://www.notion.so/Ep-4-Brad-McClleland-from-CEO-Intern-to-Robotics-to-RevOps-Business-Owner-190a0673e18f80588936fbe47fa37f9f?pvs=21]