The Journey To Legacy Blog

David Greer and Wayne Veldsman

You Don't Have to Do It Alone: Lessons in Business and Recovery from a Serial Entrepreneur

February 20, 20253 min read

In the latest episode of the Journey To Legacy podcast, host Wayne Veldsman sits down with David Greer, a remarkable entrepreneur whose story spans from building a multi-million dollar software company while battling alcoholism to finding his true calling as a coach helping other entrepreneurs overcome their own challenges.

The Accidental Entrepreneur

David's journey begins in Edmonton, Alberta, where his passion for combining computers and business emerged as early as ninth grade. Unlike many modern entrepreneurs chasing fame and fortune, David simply followed his interests, eventually becoming the first employee at Robel, a software company he would later co-own.

"I didn't have a vision of the form or what it would look like," David reflects. "I just knew those two things needed to go together." For decades, despite co-owning and growing a successful global software enterprise, David still identified himself as a "computer programmer" rather than an entrepreneur.

Building Success Through Customer Focus

One of the most striking insights from David's story is how his company achieved remarkable success by maintaining an unwavering focus on customer needs. At trade shows, rather than launching into product demonstrations, David would spend time understanding potential customers' environments, teams, and challenges. He would then demonstrate only the 5% of their product that directly addressed those specific needs.

This customer-centric approach, combined with a commitment to quality and innovation, helped Robel become an industry leader. The company was known for consistently delivering annual updates to all their products – a feat their competitors struggled to match.

The Hidden Struggle

Behind this success story lay a darker reality. For over 20 years, David was what he calls a "high-functioning alcoholic." He used alcohol to cope with both failures and successes, drinking to feel better when things weren't going well and to amplify the highs when they were.

"I got sick and tired of being sick and tired," David shares, describing the moment he finally decided to seek help. Through working with a business coach, Kevin Lawrence, David eventually confronted his alcoholism and attended his first AA meeting on January 27th, 2009.

From Personal Growth to Professional Impact

David's recovery journey transformed not just his personal life but his professional approach as well. After getting sober, he discovered that his own growth and healing enabled him to better serve others as a coach.

"We can only show up for our clients as well as we have done our own personal growth," David explains. Each layer of self-discovery and healing has enhanced his ability to ask deeper questions and recognize patterns in his clients' behaviors and challenges.

Key Lessons for Entrepreneurs

Throughout the conversation, several valuable insights emerge for business owners:

  1. Don't Do It Alone: David emphasizes that while many entrepreneurs resist help (he estimates 95%), trying to "haul big rocks around on your own" isn't necessary or effective.

  2. Strategic Vision Matters: Using the Scaling Up framework, David helps clients look three years ahead and work backward to create actionable quarterly plans – a more effective approach than the traditional "let's do 10% better than last year" method.

  3. Listen to Your Market: Success comes from deeply understanding customer needs and focusing solutions on those specific requirements rather than showcasing every feature you've built.

Creating a Meaningful Legacy

Today, David's legacy centers on sharing his "experience, strength, and hope" in both business and recovery. He specializes in working with entrepreneurs who face addiction challenges, bringing a unique understanding to both the professional and personal aspects of their struggles.

"The businesses only grow as fast as they themselves can grow," David notes, highlighting why personal development is crucial for entrepreneurial success. His story demonstrates how confronting our deepest challenges can become the foundation for helping others overcome theirs.


If you're an entrepreneur seeking guidance or struggling with addiction, David welcomes you to reach out through his website for a free one-hour coaching call. Sometimes the bravest thing we can do is admit we don't have to do it all alone.

Listen to the full episode of Journey To Legacy with David Greer to hear more insights about entrepreneurship, recovery, and building a meaningful legacy through helping others.

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Wayne Veldsman

Wayne Veldsman, owner of Vel.Consulting and Journey To Legacy is an accomplished online business growth strategist, success coach, and entrepreneur. He specializes in helping global nonprofit organizations to change the world by helping them grow both their mindsets and their NPO's revenue. After starting his first business in 2014, Wayne successfully launched and scaled a digital marketing agency to a 7-figure valuation before deciding to exit in 2019 to move to Denver, Colorado and start chasing his passion of coaching and public speaking. Wayne actively works with executive directors, entrepreneurs and businesses who are looking to take massive action and create drastic changes in their lives.

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