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
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:
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/
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/
GrowthRise – Community for B2B sales & marketing leaders: https://www.growthrise.com/
Ryan’s LinkedIn: 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)
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)
Contact Ryan: ryan@saasrise.com
Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/
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/
Read Alec’s book Workflow Modeling:Workflow Modeling: Tools for Process Improvement and Application Development, 2nd Edition
Connect with Alec Sharp:
https://www.linkedin.com/in/alecsharp/
LucidChart Webisodes series on process mapping methodology:
https://youtube.com/playlist?list=PLUr2vo1BNYKWYrzCjCXmYXimCOFTWDTaB&si=tauHVuIhC4VSXNSs
Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn:
In this episode of How I Started, host Andrew Kappel interviews Greg DiFraia, the CEO of Inlayer and a longtime technology leader with a career spanning Dell EMC, Turbonomic, Scality, and beyond. Greg shares his remarkable journey from starting in sales and operations roles at small tech resellers to leading emerging technology groups inside one of the world’s largest tech companies—and eventually stepping into the CEO seat at a fast-growing startup.
Greg dives into the experiences that shaped his leadership philosophy, including the critical role of mentorship, the importance of building deep technical knowledge even with a marketing degree, and how he navigated the transition from big corporate environments to scrappy startup life.
He also shares his philosophy on building company culture, scaling innovation, the reality of raising capital as a CEO, and why relentless self-development is at the core of his career journey.
Greg’s story offers incredible insights for anyone passionate about leadership, technology innovation, startups, or personal growth.
Takeaways
- Greg started his tech career in Rhode Island, working for value-added resellers before moving to Dell EMC.
- Transitioned from a marketing background to technical leadership by investing in certifications, mentorship, and relentless self-education.
- Helped scale Dell EMC through major milestones, including the VMware acquisition and rapid employee growth.
- Embraced the startup world with Turbonomic and Scality, helping companies innovate, grow alliances, and drive strategic partnerships.
- Took the leap to an early-stage company, now leading Inlayer’s growth as CEO.- Highlights the importance of networking, mentorship, and proactive career planning.
- Shares how startup leadership requires flexibility, relationship-driven execution, and personal ownership of company success.
- Talks about building work culture that is both performance-driven and deeply human-centered.- Focuses on constant learning—even (and especially) when outside the comfort zone.- Believes in balancing professional ambition with intentional personal growth and life balance.
Chapters
00:00 – Welcome to Rhode Island and Greg’s Career Overview
01:45 – Starting in Tech with Resellers and Integrators
03:30 – Moving from Marketing Degree to Technical Roles
06:00 – Scaling with Dell EMC and Mentorship Lessons
08:45 – Transitioning to Startups: Turbonomic and Scality
11:30 – Joining Early-Stage Companies and Building from Scratch
14:00 – Challenges and Opportunities of Startup Leadership
16:45 – Building a Strong Company Culture and Team
19:20 – Developing New Skills as a First-Time CEO
21:00 – Managing Growth, Fundraising, and Personal Development
23:30 – Work-Life Balance Challenges at High-Growth Companies
26:00 – Where to Learn More About Inlayer
Leadership, technology startups, career growth, mentorship, innovation, tech sales, startup CEO, professional development, Inlayer, network management, venture capital, self-development, technical sales, Rhode Island tech, EMC, Dell EMC, Turbonomic, Scality, startup culture, entrepreneurship, SaaS, API platforms, human-centered leadership, How I Started Podcast, career planning, building companies, executive leadership, scaling startups, emotional intelligence
📍 Learn more about Inlayer: https://inlayer.com/
🌐 Learn more about Phonism (product): https://phonism.com/
🔗 Connect with Greg DiFraia: https://www.linkedin.com/in/greg-difraia-7914704/
In this episode of How I Started, host Andrew Kappel interviews Barry Rhein, the founder of Selling Through Curiosity and a faculty member at Stanford Business School. Barry shares his unorthodox journey from teenage entrepreneur with no college degree to becoming a renowned sales trainer and educator for Silicon Valley’s top companies.
Barry dives into the personal and professional experiences that shaped his life—from selling fishing worms and training dogs as a kid, to being fired repeatedly for questioning traditional sales models. He eventually launched his own sales training business built on an audacious offer: "Only pay me if you get results."
His curiosity-based method became a powerful tool not just for selling, but for coaching, managing, hiring, and leading. Barry has trained teams at companies like Salesforce and HP, pioneered virtual sales training long before Zoom, and now teaches Stanford MBAs how to master human connection through practical, hands-on exercises.
Barry is currently working with his daughter on a new project: Dating Through Curiosity, applying B2B sales techniques to personal relationships—and plans to expand into Parenting Through Curiosity next.
Takeaways
- Barry began his entrepreneurial journey at 12, persistently seeking jobs, selling worms, and studying behavior through dog training.
- He entered sales without a college degree and got fired multiple times for challenging the status quo.
- Created Selling Through Curiosity—a method that emphasizes authentic connection and curiosity-driven conversations.
- Built his business on outcome-based pricing: clients only pay if they get results.
- Was invited to Stanford after success at Salesforce, later co-developing a practice-based MBA course in sales.
- Pioneered virtual breakout rooms and remote training years before it became the norm.
- Has trained hundreds of thousands globally, scaling through innovation and adaptability.
- Currently working on Dating Through Curiosity, applying sales skills to personal connection and relationships.
- Emphasizes overcoming limiting beliefs, finding commonality, and connecting with authenticity.
- His philosophy: Sales is life—it’s not just about closing deals, it’s about helping people reach positive conclusions.
Chapters
00:00 – Intro to Barry Rhein and Early Hustle Stories
01:45 – Selling Worms, Dog Training, and Studying Human Behavior
03:10 – Becoming a Police Officer, Then Pivoting to Sales
04:50 – Getting Fired for Insubordination—and Why That Was a Good Thing
07:25 – Launching Selling Through Curiosity with “Only Pay If It Works”
09:30 – Training Teams at Salesforce, HP, and More
11:00 – Earning a Spot at Stanford Without a Degree
13:45 – Building the MBA Course: Hands-On, Practical Selling
16:05 – Virtual Training Innovation Before Zoom
18:20 – Impact at Scale: Training Over 100,000 People
20:10 – New Chapter: Dating Through Curiosity
22:00 – Future Vision: Parenting Through Curiosity
24:30 – Mentors, Inspiration, and the Power of Action
26:00 – Where to Find Barry Online and What’s Next
Keywords
Sales training, curiosity, human behavior, leadership, entrepreneurship, communication skills, Stanford MBA, Selling Through Curiosity, remote training, virtual sales, business development, coaching, recruiting, relationship building, personal growth, limiting beliefs, Dating Through Curiosity, Parenting Through Curiosity, outcome-based consulting, authenticity, sales philosophy, edtech, life skills, professional development, emotional intelligence, influence, connection, podcast
Selling Through Curiosity Website (STC): https://barryrhein.com/
Instagram- Through Curiosity: https://www.instagram.com/through.curiosity/?hl=en
LinkedIn: https://www.linkedin.com/in/barry-rhein-1b6123/
Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/
In this episode of How I Started, host Andrew Kappel interviews Matt Bolian, co-founder of Supered, a platform focused on transforming service delivery for HubSpot partners and beyond. Matt shares his unique journey from West Point graduate and military intelligence officer to revenue operations leader, agency founder, and now tech entrepreneur.
Matt dives into the lessons learned from his time in the military, including pattern recognition, decision-making under uncertainty, and leadership in high-stakes environments—skills that later shaped his approach to RevOps and business consulting. He talks about launching and scaling RevPartners, one of the fastest-growing HubSpot partner agencies, and the insights that led him to create Supered. The conversation covers tech-enabled service delivery, the challenges of scaling service businesses, and his goal of building a $100 million company without VC funding.
Takeaways
- Military training in prioritization, failure, and pattern recognition directly influenced Matt’s approach to business problem-solving.
- Transitioning from the Army to private sector tech required learning the differences between project management and RevOps leadership.
- His experience integrating ERP and CRM systems sparked his interest in RevOps consulting.
- Founding RevPartners demonstrated the power of operational efficiency and outcome-based consulting models.
- The limitations of scaling service companies led to the creation of Supered, focused on increasing delivery capacity per head.
- Supered aims to enable next-gen HubSpot partners by offering tech-enabled solutions that enhance service quality and partner profitability.
- Matt emphasizes bootstrapping and maintaining control and ownership as a key part of his long-term strategy.
- Mentorship, adaptability, and lifelong learning are recurring themes in Matt’s career evolution.
- His vision includes expanding Supered beyond HubSpot partners to end users, targeting $100 million in revenue.
Chapters
00:00 – Introduction to Matt Bolian and His Career Journey
01:11 – West Point, Leadership Training, and Early Lessons
03:24 – Becoming a Military Intelligence Officer: Pattern Recognition and Predictions
07:08 – Forecasting, Decision-Making, and High-Stakes Scenarios
09:00 – Six Years in the Army: Command Roles and Multinational Logistics
10:56 – Transitioning from Military to Civilian Tech: A Rough Start
12:24 – Chief of Staff at C Spire: Entering RevOps and Channel Management
14:55 – Revenue Systems, M&A Integration, and Building Processes
17:36 – Moving to PE-Backed Companies and Running Business Ops
20:04 – Founding RevPartners: Standardizing on HubSpot
22:17 – Rapid Growth and SaaS-Like Scaling in an Agency Model
23:50 – The Challenges of Service Delivery and Client Experience
25:15 – Birth of Supered: Increasing Capacity Without Adding Headcount
27:01 – Building the Next Generation of Elite HubSpot Partners
28:50 – Long-Term Vision: Serving End Users and Scaling to $100 Million
29:38 – Bootstrapping Supered and Building a Winning Culture
30:02 – Where to Find Matt: LinkedIn and Supered.io
Keyword
RevOps, Revenue Operations, HubSpot, CRM, Service Delivery, SaaS, Entrepreneurship, Military Leadership, Business Operations, Process Optimization, Private Equity, Tech Consulting, Salesforce, Microsoft Dynamics, Pattern Recognition, Forecasting, ERP Systems, Agency Scaling, Bootstrapping, Supered, RevPartners, Channel Management, SaaS Growth, Leadership Development, Mentorship, Service Innovation, End Users, HubSpot Partners, Scaling Service Businesses
Connect with Matt on LinkedIn:
https://www.linkedin.com/in/matthewbolian/
Supered Website:https://www.supered.io
Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/
In this episode of How I Started, host Andrew Kappel interviews Brad McClelland, founder of RevenueForce.io, a consulting firm specializing in RevOps and commercial maturity. Brad shares his unconventional career journey, from working at a tech startup, PeopleMatter, to leading sales at a cell phone repair franchise, and then transitioning into consulting for private equity-backed SaaS and services companies.
He discusses the power of mentorship, the importance of process optimization, and how his experience across B2B, B2C, consulting, and even robotics has shaped his approach to solving business challenges. The conversation also explores the trade-offs between full-time employees vs. contractors, the role of RevOps in scaling companies, and how private equity firms approach revenue growth strategies.
Takeaways
- Early exposure to executive leadership helped Brad develop business acumen quickly.
- Being part of an early-stage SaaS company provided insight into startup growth and sales enablement.
- Transitioning into B2C (franchises and repair services) offered a new perspective on operations and profitability.
- Private equity-backed companies prioritize process optimization and efficiency in revenue operations.
- Building RevOps functions from scratch requires strategic planning and deep understanding of systems like Salesforce and HubSpot.
- The contractor model can be more effective than hiring full-time employees in consulting.
- Revenue growth in PE-backed companies requires a blend of data-driven decision-making and operational expertise.
- Experience across multiple industries allows for cross-pollination of best practices.
- Mentorship is critical for career growth, and Brad credits three major mentors for shaping his journey.
- Downtime in business—whether in retail, consulting, or labor efficiency—is a cost killer.
Chapters
00:00 – Introduction to Brad McClelland and His Career Journey
01:49 – Early Experience at PeopleMatter: Learning from Leadership
04:14 – Transition to Franchise Sales: Scaling a B2C Business
07:43 – The Role of Operational Efficiency in Business Growth
12:18 – Side Quest: Brad’s Venture into Industrial Robotics
14:24 – Meeting Andrew & Working at Skaled Consulting
17:20 – Founding Revenue Force: Focus on RevOps & Commercial Maturity
19:09 – Working with Private Equity Firms and Portfolio Companies
22:29 – The Role of Reporting & Data in Revenue Operations
22:44 – Closing Thoughts and Where to Find Brad
Connect with Brad on LinkedIn:
https://www.linkedin.com/in/bradmcclelland/
Revenue Force Website:
Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/
In this episode, Andrew Kappel interviews Jeffrey Moss, the founder of Parker Dewey, a company focused on bridging the gap between college and career through micro internships. Jeffrey shares his journey from investment banking to education technology, highlighting the challenges students face in securing internships and the biases employers have in hiring. He discusses the inception of Parker Dewey as a solution to these issues, creating low-stakes opportunities for students to gain experience while providing employers with a better way to assess talent.
The conversation also touches on the growth of the company and the future of micro internships in the recruiting landscape. In this conversation, Jeffrey and Andrew discuss the growing trend of integrating micro internships into the recruitment process, particularly focusing on the unique skills that student athletes bring to the table. They explore how companies are leveraging these internships to create equitable pathways for students while also benefiting from the fresh perspectives that college students offer. The discussion highlights the importance of mentorship, relationship building, and the role of established companies like IBM and HubSpot in supporting these initiatives. The conversation wraps up with insights on entrepreneurship and the significance of simplicity in business processes.
Takeaways
• Micro-internships provide valuable experience for students.
• Employers often rely on biases in hiring processes.
• Parker Dewey was created to address the college to career gap.
• Students need low-stakes opportunities to explore career options.
• The concept of micro-internships is gaining traction.
• Employers benefit from engaging with students early on.
• Real-world experience is crucial for career readiness.
• The platform has partnerships with over 900 colleges.
• The future of recruiting will include more experiential learning opportunities. Companies are increasingly integrating micro internships into their recruitment processes.
• Student athletes possess valuable skills such as grit, determination, and coachability.
• Micro internships provide a bridge between education and industry, offering real-world experience.
• Programs funded by major companies like IBM are creating opportunities for students to gain skills in AI.
• Networking through projects can help students build valuable professional relationships.
• Simplicity in business processes is crucial for scalability and success.
• Mentorship is a two-way street, benefiting both students and professionals.
• The demand for micro-internships is high, with many companies participating.
• Understanding the patterns of success and failure in entrepreneurship is key to growth.
Chapters
00:00 - Introduction to Jeff Moss and Career Pathways
12:03 - Creating Low-Stakes Opportunities for Students
15:04 - The Value Proposition for Employers
17:53 - Growth and Evolution of Parker Dewey
20:53 - Looking Ahead: The Future of Micro Internships
22:49 - Integrating Micro Internships into Recruitment
24:47 - The Value of Student Athletes in Business Development
26:59 - Micro Internships: Bridging Education and Industry
29:39 - Finding Opportunities in Micro Internships
32:13 - Building Relationships Through Projects
34:59 - Insights from Successful Entrepreneurs
Connect with Jeffrey on LinkedIn:
https://www.linkedin.com/in/jeffreybmoss/
Parker Dewey Website:
Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/
In this episode, Andrew Kappel interviews Omeed Tabiei, a lawyer and entrepreneur, who shares his unexpected journey from aspiring public defender to multi-time startup founder, and now law firm owner. Omeed discusses the serendipitous events that shaped his career, his experiences in politics and tech, and the lessons learned from his entrepreneurial ventures.
He emphasizes the importance of quick wins, the iterative nature of starting a business, and reflects on how he would have approached his career differently. The conversation highlights the intersection of law and entrepreneurship, providing valuable insights for aspiring founders and legal professionals alike.
Takeaways
Omeed never intended to own a law firm, highlighting the unpredictability of career paths.
Omeed became fascinated with business serendipitously while working as a political aid in Washington DC.
Starting a business and entrepreneurship in general is an iterative process filled with failures and lessons.
00:00- The Unexpected Journey to Law Firm Ownership
05:34- From Politics to Tech: A Shift in Focus
11:31- The Entrepreneurial Spirit Awakens
18:12- Lessons from Failed Ventures
24:28- Building a Successful Law Firm
30:21- Reflections on the Journey and Future Aspirations
Connect with Omeed on LinkedIn:
https://www.linkedin.com/in/omeed-tabiei/
Optimist Legal Website:
Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/
In this inaugural episode of the How I Started Career Stories podcast, host Andrew Kappel interviews Dan Currin, co-founder of OrgChartHub and GeoMapper. Dan shares his entrepreneurial journey, starting from his early aspirations in university, through his experiences at Enterprise Rent-A-Car, and into the startup world. He discusses the importance of cultural exposure, the challenges of transitioning from a corporate job to a startup, and the lessons learned from his various ventures. The conversation highlights the significance of patience and understanding customer needs in building successful businesses, as well as the exciting future ahead for OrgChartHub and GeoMapper.
Takeaways
- **01:27** Early Aspirations and University Experience
- **04:17** Cultural Exposure and Entrepreneurial Seeds
- **06:38** Enterprise Rent-A-Car: A Learning Experience
- **10:04** Transitioning to Startups and New Ventures
- **13:34** From Idea to Business: The Birth of OrgChartHub
- **15:57** Lessons Learned from Past Ventures
- **17:58** Expanding the Business: GeoMapper and Future Plans
Connect with Dan on LinkedIn: https://www.linkedin.com/in/danieljcurrin/
Sign up for OrgChartHub here: https://orgcharthub.com/
Questions or Guest Ideas? Contact the Host Andrew Kappel on LinkedIn: https://www.linkedin.com/in/andrewkappel/
