Lessons by the Lake: The Oswego Private Wealth Show

Hosted by Bob Bedritis

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May 2025

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About the show

Welcome to Lessons by the Lake: The Oswego Private Wealth Show! Featuring Bob Bedritis, Managing Director of Oswego Private Wealth Management, we'll explore various wealth management strategies, solutions, and conversations that Bob is discussing with his affluent clients every day. Whether it be circumstances related to family businesses, wealth preservation, or even charitable intent, this show covers a wide-variety of financial services that's bound to leave you with some considerations for your own financial portfolio. Thanks for checking out our show! Be sure to leave a comment and subscribe on your favorite podcasting platform so you never miss another episode! Enjoy!

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35 recent

May 21, 202536 min

Timing the Transition: When and How to Start Exit Planning (Feat: Scott Snider)

In this episode of Lessons by the Lake , we sit down with Scott Snider, President of the Exit Planning Institute, to explore one of the most critical—and often overlooked—phases in a business owner’s journey: knowing when and how to begin planning your exit. Scott shares expert insights on the strategic importance of timing, how early preparation creates more attractive, valuable businesses, and what missteps to avoid along the way. Whether you're a business owner considering a sale in the next few years or a trusted advisor to one, this conversation offers practical frameworks and real-world examples to help guide successful transitions. Chapters: 0:00 - Introduction 3:23 - The exit planning process 8:01 - The owner readiness survey findings 19:14 - When to begin the exit planning process 28:39 - Finding your meaning and purpose 33:32 - How to get in touch with Bob and his team 34:44 - Closing remarks

April 7, 202537 min

Driving Untapped Growth and Resilience for Business Owners (Feat: Rick Campfield)

In this episode of Lessons by the Lake , we sit down with Rick Campfield, a seasoned business executive turned consultant and coach, to uncover the hidden drivers of growth and resilience for today’s business owners. With decades of leadership experience under his belt, Rick shares how he now guides entrepreneurs through their most pressing personal and professional challenges. From navigating uncertainty to fostering sustainable growth, Rick's insights offer a powerful blend of strategic thinking and personal development. Whether you’re a startup founder, small business owner, or executive leader, this conversation will leave you with tangible tools and a renewed mindset to tackle what’s next. Chapters: 0:00 - Introduction 3:26 - Rick's background and early career path 13:39 - Vision, mission, purpose and objectives 20:43 - The importance of leveraging great counsel 31:09 - An important realization business owners arrive to 34:45 - How to get in touch with Rick and Bob's respective teams 35:28 - Closing remarks

March 24, 202535 min

Navigating Business Sales for Maximum Gain (Feat: Johnathan Choe)

In the latest installment of Lessons by the Lake , we dive into the complex world of business sales with expert guest Johnathan Choe, President and Lead Advisor at Transworld Business Advisors of Oregon Central. Whether you're planning an exit strategy, preparing to sell, or just exploring future possibilities, this episode is packed with actionable insights to help business owners maximize value and navigate the sales process with confidence. Join us as we explore key considerations, common pitfalls, and winning strategies for selling a business in today’s market. Don’t miss this essential conversation for entrepreneurs, investors, and anyone looking to make the most of their business transition. Chapters: 0:00 - Introduction 3:52 - Who Johnathan and Transworld typically work with 12:20 - Helping business owners prepare for sale 22:49 - Common misconceptions among business owners 31:02 - Working with a team of professionals 33:30 - Closing remarks

February 10, 202532 min

Leverage Accurate Accounting to Drive Efficient Strategy

In the latest installment of Lessons by the Lake: The Oswego Private Wealth Show , we sit down with Carl J. Cox, Founder of 40 Strategy and 40 Accounting, for an insightful conversation on the power of accurate financial data in driving business success. Carl shares his expertise on how leveraging precise accounting information can lead to more efficient decision-making, better strategic planning, and ultimately, stronger financial outcomes. Whether you're a business owner, executive, or entrepreneur, this episode offers valuable takeaways on aligning your numbers with your vision to achieve sustainable growth. Tune in for practical strategies and expert insights that can help you navigate financial complexities with confidence. Chapters: 0:00 - Introduction 3:20 - Carl's background in strategy and accounting 10:09 - The marriage of 40 Strategy and 40 Accounting 18:34 - The exit planning reality check 30:02 - How to get in touch with Carl and Bob

December 9, 202422 min

Avenues of Opportunity: SBA Loan Strategies for Business Owners

In this episode of Lessons by the Lake: The Oswego Private Wealth Show , we’re joined by Jani Beatty, Vice President and SBA Relationship Manager at Northwest Bank. Jani shares her expertise on loan strategies tailored for entrepreneurs navigating businesses of all sizes. From securing funding for growth to leveraging Small Business Administration (SBA) loans effectively, this conversation is packed with actionable insights to help business owners optimize their financial strategies. Whether you’re launching a startup or scaling an established enterprise, Jani’s guidance will empower you to make informed borrowing decisions. Chapters: 0:00 - Introduction 4:02 - Leveraging SBA loans to grow your business 11:31 - Taking a deeper look into your business 17:09 - SBA loans vs. commercial bank loans 19:23 - Connect with Bob and his team 20:10 - Closing remarks Connect with Bob Bedritis: Website: oswegoprivatewealth.com Facebook: facebook.com/Oswego-Private-Wealth-Management-106334761908104/

October 16, 202438 min

What Is Your Game Plan? Featuring Paul Menig

In this insightful episode of Lessons by The Lake , Bob Bedritis is joined by Paul Menig, a seasoned business strategist and succession planning expert. Together, they dive into the critical steps business owners need to take to maximize the value of their companies while planning for a smooth and successful transition. Paul shares his wealth of knowledge on aligning leadership, preparing for unforeseen events, and ensuring that businesses are set up for long-term success. Whether you’re a business owner looking to transition out or just curious about what it takes to future-proof your business, this episode is packed with valuable advice and actionable insights. Tune in for a deep conversation about planning for the future, keeping stakeholders aligned, and ensuring that you leave a lasting legacy. Chapters: 0:00 - Introduction and overview on the topic of the show 2:20 - Welcoming Paul Menig 3:00 - The Game Plan 5:50 - Executing as a Team and as Individuals 08:20 - The Forces That Impact Businesses 11:40 - People Power 16:10 - Why 'Why' Comes First 21:50 - Where to Improve First 25:30 - Visual Instruction vs. Verbal 32:00 - Trucking and Tracking 35:00 - Closing Remarks and How to Get in Touch with Paul Menig 35:30 - How to get in touch with Bob's team Connect with Paul: Website: Businessaccelerants.com Connect with Bob Bedritis: Website: oswegoprivatewealth.com Facebook: facebook.com/Oswego-Private-Wealth-Management-106334761908104/

October 7, 202437 min

The Founder's Journey with David Howitt

In this episode of Lessons by the Lake, Bob Bedritis sits down with David Howitt, founder and CEO of the Merriweather Group, to explore "The Founder's Journey." David, a visionary entrepreneur and author, has dedicated his career to helping businesses merge purpose with profit. Through the Merriweather Group, he supports passionate founders and leaders in creating companies that balance commerce and creativity. In this inspiring conversation, David shares his own entrepreneurial journey—the challenges, triumphs, and invaluable lessons he's learned along the way. Whether you’re an aspiring entrepreneur or a seasoned business leader, David's insights on building a purpose-driven business and embracing authenticity are sure to resonate. Tune in for a deep dive into what it really takes to build a successful company while staying true to your values. Chapters: 0:00 - Introduction and overview on the topic of the show 2:20 - Welcoming David Howitt 4:00 - The Journey 5:50 - Dave's Bread 11:10 - The Abyss 15:15 - Scaling Despite Difficulty 18:50 - Human Connection 22:00 - Macro and Micro Journeys 26:40 - Higher Purpose and Community 29:40 - The Space Between 31:15 - Mentorship and Vision 34:50 - How to get in touch with Bob's team Connect with Bob Bedritis: Website: oswegoprivatewealth.com Facebook: facebook.com/Oswego-Private-Wealth-Management-106334761908104/

September 16, 202431 min

Is Your CPA an Advisor or a Historian? (Feat. Robert Curtis, CPA)

On the latest episode of Lessons by the Lake, we're discussing the intersection of wealth management and accounting with Robert Curtis, CPA. As the founding member of Neumann Curtis CPA's, Robert speaks intimately on the true role of a great advisor. This episode is packed with some helpful takeaways for your own financial world, so get your notepad ready! Chapters: 0:00 - Introduction and overview on the topic of the show 3:20 - Welcoming Robert Curtis, CPA 9:00 - The Neumann Curtis Niche 14:10 - One Size Does Not Fit All 17:10 - Asking the Right Questions 19:40 - Communication at The Client Perspective 23:10 - Exit and Succession Planning 25:40 - Proactive Advisor vs. Historian 28:50 - How to Get in Contact with Rob 29:35 - How to get in touch with Bob's team Connect with Bob Bedritis: Website: oswegoprivatewealth.com Facebook: facebook.com/Oswego-Private-Wealth-Management-106334761908104/

August 26, 202429 min

Build a Business With Real Intrinsic Value with Craig Wigginton

On the latest episode of Lessons by the Lake, we're examining a widely discussed but little understood topic among entrepreneurs and business leaders. We we fortunate to welcome Craig Wigginton, professional EOS implementer. Craig helps entrepreneurial leadership teams get what they want out of their businesses through the implementation of the Entrepreneurial Operating System. Through education, coaching, and facilitation, he has helped dozens if not hundreds of business make the etherial word vision, a reality. This episode is packed with some helpful takeaways for your own financial world, so get your notepad ready! Chapters: 0:00 - Introduction and overview on the topic of the show 2:00 - Welcoming Craig Wigginton 6:00 - Habits 10:30 - The Magic's in The Details 13:00 - The Glass Ceiling of Individual Performance 15:30 - Communication is What You Hear 18:00 - The Tools of Successful Delegation 20:40 - The Most Common Bad Habits 23:20 - Systemized Kind Communication 25:00 - Closing Remarks 26:35 - How to get in touch with Bob's team Connect with Bob Bedritis: Website Facebook YouTube

June 10, 202431 min

The Strategic Pillars of Wealth

On the latest episode of Lessons by the Lake, we're diving deep into the core concepts surrounding wealth management, as well as the most prevalent concerns facing business owners and their financial world. We we fortunate to welcome Joe Jraitiny, Managing Director at City National Rochdale, to discuss these five pillars of wealth and how his team plays a crucial role in upholding these pillars for clients nationwide. This episode is packed with some helpful takeaways for your own financial world, so get your notepad ready! Chapters: 0:00 - Introduction and overview on the topic of the show 2:07 - Bob's relationship with Joe Jraitiny 6:37 - The Five Strategic Pillars of Wealth 9:57 - Leveraging the expertise from a team of advisors 12:06 - An area of your financial world that is often overlooked 17:32 - The ideal timeframe for thinking about selling your business 22:21 - Longevity planning and where this fits in your financial world 26:08 - How you can get in touch with Joe and his team at City National Rochdale 28:35 - How to get in touch with Bob's team 29:07 - Closing remarks Connect with Bob Bedritis: Website Facebook YouTube