Episode 008: Overcoming Career Transitions with Len Ward

What happens when the security of corporate America no longer feels aligned with your future? In this episode of Overcoming Anything, I sit down with Len Ward, entrepreneur and founder, who shares his journey of leaving a steady paycheck behind to step into the uncertainty of business ownership.

From the fear of supporting a young family, to losing his first business during the 2008 housing crisis, to rebuilding with resilience and scaling a successful digital agency, Len’s story is a powerful reminder that courage, action, and self-belief are the foundation of any entrepreneurial journey.

Len also shares why paying yourself first matters, how to manage imposter syndrome, and why AI-enabled small businesses will be the future.

Len Ward is the Managing Partner of Commexis, an AI consulting and product development firm helping businesses evolve into AI-native organizations. A former Wall Street VP at Morgan Stanley and Credit Suisse, Len transitioned from finance into entrepreneurship during the dot-com boom, launching an e-commerce business and self-teaching digital growth. He went on to build and scale a full-service marketing firm and today leads a team creating AI-powered marketing engines, intelligent chatbots, and workflow automation tools.

Key Takeaways

1. Indecision will kill you- Success comes from taking action quickly and course correcting along the way, rather than staying stuck in fear or hesitation.
2. Pay yourself first- Even if it’s a small percentage, prioritizing your own paycheck from day one ensures sustainability and prevents the “vanity growth” trap many entrepreneurs fall into.
3. Failure fuels growth- Losing a business isn’t the end—it’s the training ground that equips you with the resilience, knowledge, and confidence to build something stronger.

Timestamps

00:00 — Welcome & introduction
03:10 — Len’s mantra: “Indecision will kill you”
07:00 — Leaving corporate America with a young family
11:20 — The challenge of paying yourself first
15:45 — Loneliness and self-reliance in entrepreneurship
20:00 — The 2008 collapse and losing his first business
24:30 — Starting again: free work, first clients, and the “unplugged phone” moment
30:00 — Scaling from solopreneur to 25 employees (and what broke)
37:00 — Key merger that changed everything
42:15 — Facing imposter syndrome and believing in yourself
48:30 — How AI will reshape small business and entrepreneurship
55:00 — Lessons learned, books that made a difference
01:02:00 — Where to connect with Len

Connect with Len Ward

Website: Commexis.com
LinkedIn: Len Ward
Twitter/X: @LenWardNJ

Books & Resources Len Recommends

• The E-Myth Revisited — Michael Gerber https://a.co/d/781knp4
• Purple Cow — Seth Godin https://a.co/d/5RpaepW
• The Untethered Soul — Michael A. Singer https://a.co/d/75Q2FMR
• Everyday AI podcast

Credits

• Host: Anne Vryonides
• Guest: Len Ward

DisclaimerDisclaimer

The content of this episode is for informational and inspirational purposes only. It is not a substitute for professional advice, therapy, or coaching.

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❤️ Anne