The Art of Succession

About The Art of Succession

Stepping into the role of business owner is one of the most challenging endeavors you'll undertake. Buying that business from someone you already know amplifies the risk of mistakes. On The Art of Succession Podcast, you'll hear from entrepreneurs who've successfully transitioned from employee to owner by acquiring businesses from parents, former bosses, or co-founders. Together, we'll explore how they navigated the complex blend of emotions and strategic decisions required to honor the past while forging a new and vibrant future. Your host, Barrett Young, a fellow traveler in the succession story of a 75+ year CPA firm himself, invites his guests to reflect on the mindset shifts, challenges, and triumphs that have empowered them to build on their established foundations. Whether you're just starting out or already envisioning your own succession plan, you will find insights and actionable advice to guide your journey.

Publisher

Barrett Young | GWCPA

Category

business · business

Language

en

Explicit

No

First episode

28 Jun 2024

Latest episode

20 Oct 2026

Latest episodes

59 episodes in the feed.

1. 

   20 Oct 2026

   Stop Targeting Customers and Start Solving Problems with Joseph Rockey Jr

   This GPT has already supported hundreds of multi-generational businesses through complex transitions, and I’ve translated that experience into a free Custom GPT available on our website. Explore it here: https://bit.ly/art-of-succession-our-GPT (https://bit.ly/art-of-succession-our-GPT)------------------------------------------------ Want to be a guest on our podcast? Apply and share your expertise with our audience at https://www.podmatch.com/member/artofsuccession (https://www.podmatch.com/member/artofsuccession)------------------------------------------------ Welcome to The Art of Succession Podcast. Host Barrett Young, CPA, talks with Joseph Rocky Jr,, Founder of Elite Business Cruise & Events, Keynotes & VIP Days — Decisions Without Pressure at Elite Business Conversations. Joseph shares how his career in commission-only sales led him to start his first business in 2011, build real estate ventures, and develop companies designed to operate without the owner being trapped in day-to-day work. Joseph explains how he learned to focus on the highest-value work, identify specific customer problems, and build sales systems around win-win outcomes. He also discusses how narrowing the target audience, designing roles around the right people, and aligning employee incentives with client needs helped him create businesses that could run with less owner involvement. He further discusses how business owners can prepare a company for sale or absentee ownership before pressure forces the decision. Joseph explains why selling should be a logical decision made well in advance, how buyers compare a business against other investment options, and why owners lose control once a sale closes. Joseph also shares how he evaluates whether to retain, sell, outsource, partner, or build capabilities inside a company. He connects those decisions to succession risk, supplier dependence, scaling constraints, and the importance of building a business that can keep operating without the founder at the center. Key Takeaways: Joseph started his first business in 2011 after realizing he wanted more control over the product he sold and the long-term value of his work. His early real estate ventures taught him to focus his effort on the most important driver of profitability: the purchase price. Joseph built a rent-to-own model around people going through divorce who wanted stability and a path back to homeownership. He trains salespeople to focus on solving real problems instead of forcing transactional sales. Buyers compare a business against many other investments, not only against similar companies in the same industry. A company becomes more valuable when it can operate without the owner’s time, energy, or daily involvement. Here are a few quotes from the episode: "A lot of what my world is building the business so that the owner doesn't have to be trapped in it." - Joseph Rockey "The number one determinant of what the profitability was or wasn't going to be was how much did you buy the house for in the first place?" - Joseph Rockey "If you have to do it today, you are going to lose." - Joseph Rockey "If you're making it in the moment, you're making an emotional decision for something that should be a logical-based answer, just outright." - Joseph Rockey "If you don't want to see them be successful, you shouldn't have them in your life for whatever reason that is." - Joseph Rockey Join Joseph Rockey as he shares how he moved from commission-only sales into building multiple businesses, starting in real estate. He breaks down reducing owner dependence, solving specific problems, focused roles, and systems that let employees and clients succeed together. He also covers exit timing, ownership control, buyer expectations, and supplier relationships, showing why succession planning starts long before a sale, and why strong companies run without the founder making every call. Episode Highlights [00:00] - Trailer & Introduction to Joseph [02:24] - Introducing Joseph Rocky Jr and Elite Business Conversations [02:52] - Building a business the owner does not have to be in unless they want to be [03:25] - Joseph’s start in commission-only sales and real estate [06:09] - Joseph’s first time being “The boss” [08:54] - Using a spreadsheet to work backward from profitability [16:28] - Discussing Joseph narrowing the target market around a specific customer problem [21:01] - Training salespeople to solve problems instead of forcing transactions [36:08] - Why sales decisions should be made before the moment arrives [42:01] - Scaling challenge: finding the right suppliers [51:23] - Model that’s scaling to $1 billion [54:33] - Problem currently solving for non-profit world - the cruise aspect [01:02:53] - One thing for the successor to remember for [01:05:50] -  Closing conversation Disclosure: Portions of this episode (such as the introduction or promotional segments) use AI-generated voice narration produced under human editorial review. FOLLOW THE GUEST: LinkedIn: https://www.linkedin.com/in/joerockey/ (https://www.linkedin.com/in/joerockey/) Website: https://elitebusinesscruises.com/ (https://elitebusinesscruises.com/) Company LinkedIn: https://www.linkedin.com/company/elite-business-cruises/ (https://www.linkedin.com/company/elite-business-cruises/) FOLLOW THE HOST: LinkedIn: https://www.linkedin.com/in/barrettyoung (https://www.linkedin.com/in/barrettyoung) Company LinkedIn: https://www.linkedin.com/company/gwcpa/ (https://www.linkedin.com/company/gwcpa/) Website: https://gwcpas.com/ (https://gwcpas.com/) Email: bey@gwcpas.com (mailto:bey@gwcpas.com) FOLLOW THE PODCAST: Apple Podcasts: https://podcasts.apple.com/us/podcast/the-art-of-succession/id1742796896 (https://podcasts.apple.com/us/podcast/the-art-of-succession/id1742796896) YouTube: https://youtube.com/@artofsuccession (https://youtube.com/@artofsuccession) Spotify: https://open.spotify.com/show/7uhogBxFKWAAetAbD8TVQR (https://open.spotify.com/show/7uhogBxFKWAAetAbD8TVQR) LinkedIn: https://www.linkedin.com/company/art-of-succession-podcast/ (https://www.linkedin.com/company/art-of-succession-podcast/) Website: https://gwcpas.com/podcast (https://gwcpas.com/podcast)

2. 

   6 Oct 2026

   Why Family Business Successions Fail Due to Emotion, Ego, and Poor Planning | Chip Scholz

   This GPT has already supported hundreds of multi-generational businesses through complex transitions, and I’ve translated that experience into a free Custom GPT available on our website. Explore it here: https://bit.ly/art-of-succession-our-GPT (https://bit.ly/art-of-succession-our-GPT) ------------------------------------------------ Want to be a guest on our podcast? Apply and share your expertise with our audience at https://www.podmatch.com/member/artofsuccession (https://www.podmatch.com/member/artofsuccession) ------------------------------------------------ Welcome to The Art of Succession Podcast (https://www.linkedin.com/company/art-of-succession-podcast/). Host Barrett Young, CPA (https://www.linkedin.com/in/barrettyoung), welcomes Chip Scholz (https://www.linkedin.com/in/chipscholz/), Founder & Owner of Scholz and Associates (https://www.linkedin.com/company/scholz-and-associates/) and author of Multiple books. Chip shares how his career in sales, lobbying, executive coaching, and years working with family owned logistics businesses shaped his views on succession. He explains why succession is about more than retirement, how the right questions help leaders make better decisions, and why planning for the future protects both the business and the family. The conversation covers leadership, family dynamics, identity, coaching, and building a meaningful legacy. Chip Scholz shares how his career in sales, lobbying, and executive coaching led him to work closely with family owned logistics businesses and their succession challenges. He explains why successful transitions require honest conversations, thoughtful coaching, and preparing both the business and the people for change. Chip also discusses family relationships, leadership, building confidence in the next generation, his Five Cs coaching framework, and why planning early helps protect both the business and the legacy. Key Takeaways: Chip Scholz shares how his career in sales, lobbying, and executive coaching led him to work with family-owned logistics businesses. Why honest conversations and thoughtful coaching help leaders prepare for successful business succession. Lessons from working with family businesses on leadership, legacy, and handing responsibility to the next generation. How his Five Cs framework helps leaders make better decisions and prepare for meaningful transitions. His work today focuses on coaching leaders, writing books, and helping business owners build lasting legacies. Here are a few quotes from the episode: “I'm either running an asset or a legacy, and I'd really rather run an asset.” - Chip Scholz “We know what to do, but we don't always do it.” - Chip Scholz “I want to remain useful.” - Chip Scholz Join Chip Scholz, executive coach and author of Handoffs: A Business Fable About an Urgent Transition Within a Family Business, as he shares lessons from sales, lobbying, executive coaching, and years of work with family-owned logistics businesses. He explains how honest conversations, thoughtful leadership, and his Five Cs framework help business owners prepare for succession, strengthen the next generation, and build a lasting legacy. Episode Highlights [00:00:00] - Teaser [00:02:08] - Introducing guest Chip Scholz [00:03:39] - Herb Scheer's choice: asset vs. legacy [00:05:09] - Herb grew Genco from $300K to $1.6B [00:07:45] - Building for external sale: board, phantom stock, strategic acquisitions [00:09:40] - Chip's backstory: from lobbyist at BFI to consultant [00:12:43] - First big break: speaking at warehousing association convention [00:14:13] - Running mastermind groups for 35+ family businesses [00:16:26] - Using DISC profiles as coaching entry point [00:18:58] - What Chip loves about family businesses: humility and legacy [00:27:43] - The family lawsuit nightmare: 17 shareholders, fired son, daughter takes over [00:29:46] - Coaching through family baggage and "boat anchor" employees [00:31:53] - Chip's rule: ask hard questions, never give advice [00:34:37] - The Five Cs framework: Context, Clarity, Conditioning, Choice, Character [00:37:02] - Applying the Five Cs to Chip's own succession: stroke, weight loss, woodturning [00:41:34] - Coaching those who don't want to retire but need a plan [00:44:26] - Chip's writing journey: 4 books in a year, sparked by Storyworth gift [00:49:46] - The "love tap": why you can't wait for a health scare to plan [00:54:41] - Three stages of retirement: vacation, depression, mission [01:00:01] - Lightning round: coffee, woodturning, red velvet, fall mornings [01:05:46] - Upcoming: "Handoffs" launch and next book inspired Disclosure: Portions of this episode (such as the introduction or promotional segments) use AI-generated voice narration produced under human editorial review. If today's conversation resonated with you, explore Chip Scholz's books below for more insights on leadership, succession, and building a lasting legacy. Small Decisions, Big Shifts: https://a.co/d/06TwM9qt (https://a.co/d/06TwM9qt) Every Dog Has Its Day: https://a.co/d/0huQdkPE (https://a.co/d/0huQdkPE) FOLLOW THE GUEST: Chip Scholz - LinkedIn: https://www.linkedin.com/in/chipscholz/ (https://www.linkedin.com/in/chipscholz/) Chip Scholz - Instagram: https://www.instagram.com/chipscholz/ (https://www.instagram.com/chipscholz/) Chip Scholz - Facebook: https://www.facebook.com/Chippturns (https://www.facebook.com/Chippturns) Chip Scholz - Thread: https://www.threads.com/@chipscholz (https://www.threads.com/@chipscholz) Chip Scholz - YouTube: https://www.youtube.com/@chipscholz1691 (https://www.youtube.com/@chipscholz1691) Scholz and Associates - LinkedIn: https://www.linkedin.com/company/scholz-and-associates/ (https://www.linkedin.com/company/scholz-and-associates/) Scholz and Associates - Website: https://scholzandassociates.com/ (https://scholzandassociates.com/) FOLLOW THE HOST: LinkedIn: https://www.linkedin.com/in/barrettyoung (https://www.linkedin.com/in/barrettyoung) Company LinkedIn: https://www.linkedin.com/company/gwcpa/ (https://www.linkedin.com/company/gwcpa/) Website: https://gwcpas.com/ (https://gwcpas.com/) Email: bey@gwcpas.com (mailto:bey@gwcpas.com) FOLLOW THE PODCAST: Apple Podcast: https://podcasts.apple.com/us/podcast/the-art-of-succession/id1742796896 (https://podcasts.apple.com/us/podcast/the-art-of-succession/id1742796896) YouTube: https://youtube.com/@artofsuccession (https://youtube.com/@artofsuccession) Spotify: https://open.spotify.com/show/7uhogBxFKWAAetAbD8TVQR (https://open.spotify.com/show/7uhogBxFKWAAetAbD8TVQR?si=56f12163da1f407a) LinkedIn: https://www.linkedin.com/company/art-of-succession-podcast/ (https://www.linkedin.com/company/art-of-succession-podcast/) Website: https://gwcpas.com/podcast (https://gwcpas.com/podcast)

3. 

   15 Sept 2026

   How We Rebuilt Our Business After Losing Key Team Members

   This GPT has already supported hundreds of multi-generational businesses through complex transitions, and I’ve translated that experience into a free Custom GPT available on our website. Explore it here: https://bit.ly/art-of-succession-our-GPT (https://bit.ly/art-of-succession-our-GPT) ------------------------------------------------ Want to be a guest on our podcast? Apply and share your expertise with our audience at https://www.podmatch.com/member/artofsuccession (https://www.podmatch.com/member/artofsuccession) Welcome to The Art of Succession Podcast. Host Barrett Young, CPA (https://www.linkedin.com/in/barrettyoung), a Tax and Marketing Partner at GWCPA (https://www.linkedin.com/company/gwcpa/), shares the firm's Quarter Three 2026 update and an honest look at the firm’s ongoing succession journey. In this episode, Barrett discusses the challenges of operating with a smaller team, the unexpected benefits of reduced capacity, and how GWCPA is becoming more intentional about the clients and services it takes on. He also explores the role of offshoring, the limitations of AI in solving current staffing challenges, developing his team into stronger tax reviewers, and the firm’s evolving vision for long-term client transformation. Barrett shares how GWCPA has responded to multiple team departures while still entering the end of tax season further ahead than ever before. He explains why the current staffing challenge is really a business model problem, how the firm is rethinking its services and capacity, and why he has temporarily stepped back into the tax reviewer role. He also discusses the future of AI and accounting, the importance of using technology to remove low-value work rather than replace human judgment, and the firm’s goal of becoming a transformational partner for business owners through succession and exit planning. Barrett also reflects on the bigger purpose behind GWCPA’s work, including the importance of developing future leaders and building a company that can continue beyond its current owners. From Katie passing all four sections of the CPA exam in six months to redefining what a long-term GWCPA client should look like, this quarter three update explores the challenges, progress, and long-term vision shaping the firm’s next chapter. Key Takeaways: Why GWCPA is intentionally staying smaller while reassessing its business model and client base. Why offshoring may play a role in GWCPA’s long-term staffing strategy, but is not a short-term solution. How GWCPA is preparing its team to become stronger tax reviewers through peer review and structured workflow. Why developing future leaders and building a company that can outlast its current owners is central to GWCPA’s succession journey. Additional Insights: Why reduced capacity can create an opportunity to become more selective about clients and services. Why GWCPA’s goal with offshoring is to elevate existing team members rather than simply replace preparation staff. What Barrett believes should define a three-, ten-, twenty-, or forty-year GWCPA client relationship. Here are a few quotes from the episode: “It’s a business model problem. It’s not a staffing problem.” - Barrett Young, CPA “The future is going to be accountants plus AI.” - Barrett Young, CPA “The tax return is a piece of what we do. It’s an entry point.” - Barrett Young, CPA Join Barrett as he shares GWCPA’s Quarter Three 2026 update and provides an honest look at the firm’s succession journey. Hear how a smaller team, staffing challenges, AI, and changing business needs are shaping the firm’s strategy. Barrett also discusses developing future leaders, redefining the client experience, and building a company that can continue creating value long after its current owners step away. Episode Highlights [00:00] - Teaser [03:06] - Why Q3 Was a Difficult Quarter [07:09] - Refocusing the Business Around the Right Clients [12:36] - Turning a Staffing Problem Into a Business-Model Problem [18:43] - The Need for Experienced Tax Reviewers [21:24] - Current Standing For The Coming Tax Season [30:55] - AI, Accounting, and the Future of Trusted Advisors [37:31] - Redefining the GWCPA Client Journey Through Succession and Legacy [47:26] - Q4 Priorities and What Comes Next FOLLOW THE HOST: LinkedIn: https://www.linkedin.com/in/barrettyoung (https://www.linkedin.com/in/barrettyoung) Company LinkedIn: https://www.linkedin.com/company/gwcpa/ (https://www.linkedin.com/company/gwcpa/) Website: https://gwcpas.com/ (https://gwcpas.com/) Email: bey@gwcpas.com (mailto:bey@gwcpas.com) FOLLOW THE PODCAST: Apple Podcasts: https://podcasts.apple.com/us/podcast/the-art-of-succession/id1742796896 (https://podcasts.apple.com/us/podcast/the-art-of-succession/id1742796896) YouTube: https://youtube.com/@artofsuccession (https://youtube.com/@artofsuccession) Spotify: https://open.spotify.com/show/7uhogBxFKWAAetAbD8TVQR (https://open.spotify.com/show/7uhogBxFKWAAetAbD8TVQR?si=56f12163da1f407a) LinkedIn: https://www.linkedin.com/company/art-of-succession-podcast/ (https://www.linkedin.com/company/art-of-succession-podcast/) Website: https://gwcpas.com/podcast (https://gwcpas.com/podcast)

Who has been a guest on The Art of Succession

Names identified in recent episode analyses. Showing up to five guests.

• Craig Paxson
• Ryan Steuer
• Brian Calvert
• Jon Morris
• Bob Labbe

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

YouTube views

10,602

Score snapshot 15 Sept 2025

Apple Podcasts (US)

5.0 / 5

6 ratings

Podcast Authority Score: 69 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

95

Social presence

0

YouTube

76

Engagement

32

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Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.

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