In this episode of The Art of Succession podcast, host Barrett Young interviews David Forster, a serial entrepreneur who successfully built and sold three companies ranging from landscaping services to a retail bike shop. Listeners gain valuable insights into how relationship-focused leadership, proper systems, and life transitions drive successful business exits and career pivots.

From The Farm to First Business Exit

David's entrepreneurial journey began with his farm upbringing, leading him naturally into the landscape industry. His first real business was a landscape maintenance and design company started in his early twenties to provide for his new family. Despite having no formal exit strategy, David built the company through exceptional work ethic and a relational approach, treating employees and customers as equals. After four successful years, an unexpected dream led to selling the business to a local competitor who valued their unique customer relationship approach and company culture over just the contract base.

Learning and Growing Through Multiple Ventures

After working for someone else and maturing personally, David started a second landscape company focused on residential design and build projects. This venture taught him to price properly, think systematically, and build intentional processes from the start. The business grew to similar team size but double the revenue of his first company. Around the four-year mark, feeling burned out, David discovered cycling during a week off and realized he wanted to share that stress-relief experience with other business owners, leading him to open a bike shop.

The Bike Shop Years and Life-Changing Events

David ran his bike shop for over seven years, learning retail operations, inventory management, and building community around cycling. However, his world changed dramatically when he became a father at 40 after discovering he and his wife had the MTHFR gene mutation affecting fertility. Tragedy struck when his wife's sister died unexpectedly two weeks after their daughter was born, followed by David's father's death nine months later. These profound losses forced David to reevaluate priorities, recognizing that retail hours weren't compatible with being the father and husband he wanted to be.

Transition to Fractional COO

David sold the bike shop to another dealer and eventually embraced fractional COO work after initially resisting the idea. His approach typically begins with a 6-12 week deep dive to establish core systems, followed by either training internal team members or providing ongoing part-time support. David focuses on overcoming team resistance by addressing consultant skepticism upfront, emphasizing he's there to make lives better through systems that create freedom rather than restrictions. His philosophy centers on checklists and processes that allow both new employees to learn and experienced ones to maintain focus when interrupted.

🎙️Full show notes, guest information, and video version of this episode available at https://gwcpas.com/blog/aos-david-forster

✍️ Leave feedback for the show. I’d love to hear your input https://quark-fir-a64.notion.site/1d9dd04222f380ae96c9caae27bc1c66?pvs=105

The Art of Succession Podcast is brought to you by GWCPA. Twice a month on https://www.youtube.com/@gwcpas, CPA and Partner Barrett Young explores the emotional and strategic challenges of leadership transition, offering honest insights and actionable advice for successors and founders.

If you've enjoyed this episode, please share it with others. It truly helps.

Disclaimer: This podcast is for informational purposes only and does not constitute legal, tax, or accounting advice. You should consult your own advisors before making decisions related to your situation. If you don’t have an advisor yet, reach out!

In this episode of The Art of Succession podcast, host Barrett Young reflects on a year of transformation and previews the future of both the show and GWCPA. Listeners will gain real-world insights into how succession planning is being put into practice inside an 80-year-old, multi-generational CPA firm.

Facing the Realities of Succession

Barrett shares the ongoing challenges GWCPA has faced in leadership transition, from unexpected health events to the loss of key staff and the pressures of staying independent in a market increasingly dominated by private equity. He discusses the importance of having a robust succession plan—not just for the business, but for the peace of mind of employees and families.

Strategies for Sustainable Business Transition

This season, Barrett and his team experimented with new approaches to client engagement, pricing, and internal systems. He details how GWCPA implemented engagement letters for every client, shifted to project-based profitability, and restructured roles to better serve clients and prepare for future leadership. The firm also began adopting the Entrepreneurial Operating System (EOS) to systematize processes and ensure the business can thrive beyond its current leaders.

Lessons Learned and the Road Ahead

Barrett reveals the outcomes of these changes, including improved client retention, higher revenue, and a renewed focus on building a business that can outlast any one individual. He announces that future episodes will provide quarterly updates on GWCPA’s real-time succession journey, offering listeners a transparent look at the challenges and victories of preparing the next generation of leaders.

For more resources and to follow GWCPA’s ongoing succession story, subscribe to our show.

🎙️Full show notes, guest information, and video version of this episode available at https://gwcpas.com/blog/aos-season-2-wrap

✍️ Leave feedback for the show. I’d love to hear your input https://quark-fir-a64.notion.site/1d9dd04222f380ae96c9caae27bc1c66?pvs=105

The Art of Succession Podcast is brought to you by GWCPA. Twice a month on https://www.youtube.com/@gwcpas, CPA and Partner Barrett Young explores the emotional and strategic challenges of leadership transition, offering honest insights and actionable advice for successors and founders.

If you've enjoyed this episode, please share it with others. It truly helps.

Disclaimer: This podcast is for informational purposes only and does not constitute legal, tax, or accounting advice. You should consult your own advisors before making decisions related to your situation. If you don’t have an advisor yet, reach out!

In this episode of The Art of Succession podcast, host Barrett Young interviews Nick Garofalo, founder of OpenHanded Wealth and former executive at Court Solutions, a payment processing company for traffic court fines that was successfully sold in 2017.

Building a Business That Solves Real Problems
Nick's father, though not tech-savvy himself, built an innovative payment processing company that transformed how people paid traffic tickets. "This internet thing is really cool," Nick recalls his father thinking, "it makes so much sense for people to be able to file court paperwork online instead of having to come stand in line." The company's success came from deeply understanding their customers' unique challenges and creating solutions that made court clerks' lives easier. "The real money comes from rich relationships with those customers, knowing the nuance of their particularities," Nick explains.

The Acquisition Journey
After Nick and his brother decided against taking over the family business, they prepared for an external sale. "We had to do a lot of cleanup and structure building to make the company appealing to an acquirer," Nick shares, noting they needed to formalize many aspects of the business that were previously based on handshakes. After rejecting an unfavorable initial offer, they connected with a consolidator who purchased the entire operation. Nick stayed with the acquiring company for nearly seven years, developing valuable skills in a corporate environment while supporting his growing family.

The Entrepreneur's Retirement Gap
Nick's experience watching his father bet everything on the business sale led him to identify a critical problem many business owners face: the post-sale income gap. "You're company's making 5 million, you're taking home 500,000... you sell it for two or three million and now you're going to have 80 or 120 grand a year in 4% income. What are you going to do?" This realization, combined with seeing his father miss opportunities for retirement planning, ultimately inspired Nick to launch his financial planning practice focused on helping entrepreneurs. "If you got into business, it wasn't so that you could work 90 hours a week at the expense of your family and friends," he advises.

🎙️Full show notes, guest information, and video version of this episode available at https://gwcpas.com/blog/aos-nick-garofalo

✍️ Leave feedback for the show. I’d love to hear your input https://quark-fir-a64.notion.site/1d9dd04222f380ae96c9caae27bc1c66?pvs=105

I'm looking to hear from 5 listeners via Zoom as I start to plan for Season 3 https://calendly.com/beygwcpas/aos-feedback

The Art of Succession Podcast is brought to you by GWCPA. Twice a month on https://www.youtube.com/@gwcpas, CPA and Partner Barrett Young explores the emotional and strategic challenges of leadership transition, offering honest insights and actionable advice for successors and founders.

If you've enjoyed this episode, please share it with others. It truly helps.

Disclaimer: This podcast is for informational purposes only and does not constitute legal, tax, or accounting advice. You should consult your own advisors before making decisions related to your situation. If you don’t have an advisor yet, reach out!