Pathfinder Legacy

What happens when the next generation comes back to the farm out of obligation instead of choice? In this episode of the Pathfinder Legacy Podcast, Heidi Olson tackles one of the most uncomfortable — and common — realities in family farming: obligation disguised as loyalty. Through a real client story, Heidi breaks down how unclear roles, unspoken expectations, and control can quietly turn success...

Aging, retirement, and caregiving are some of the most difficult conversations farm families face — not because of paperwork, but because of identity, fear, and unspoken responsibility. In this episode, Heidi Olson breaks down why these conversations are so often avoided, how informal caregiving quietly begins, and how unspoken roles can create resentment and stress inside both the family and the...

It's a new year — and for farm families, that means it's time for real planning, not resolutions that fade by February. In this episode, Heidi Olson walks through her 2026 Farm Legacy Checklist, outlining the six critical areas every operation should review annually to protect the business, the family, and the future. From balance sheets and land titles to LLCs, insurance, family roles, and schedu...

In this special holiday episode, Heidi Olson reflects on family traditions, farm memories, and the stories that shape legacy long before documents ever do. From shared meals to cold chores, these moments reveal values, roles, and expectations that matter deeply in succession planning. Because legacy isn't just written in paperwork — it lives in the stories we pass on.  For guides, checklists, and...

In Part 2, Heidi and Cory go deeper into the tax issues that directly impact agriculture: disaster relief payments, depreciation strategies, buying equipment wisely, gifting rules, estate and gift tax exemptions, and year-end planning that actually protects your farm's future. If you've ever wondered how depreciation really affects cash flow, how to avoid buying your way into a tax problem, or how...

In Part 1 of this tax-season deep dive, Heidi sits down with CPA and fellow farmer Cory Wheeler to simplify the biggest tax changes affecting rural families, small business owners, and ag producers in 2025. From overtime rules and tip taxation to 1099 pitfalls, contractor vs employee confusion, Social Security myths, paying children, and how to protect yourself during an audit — this episode break...

In Part 2, Heidi continues the conversation with Martin and Linda as they unpack more family history, the realities of running a farm after a sudden loss, caregiving across generations, and the importance of community involvement. This episode explores what it means to work hard, stay connected, raise resilient families, and intentionally pass down stories that would otherwise be lost. Their humor...

In Part 1 of this two-part conversation, Heidi sits down with Martin and Linda Hanson to explore their rich Norwegian heritage, early homesteader stories, and what farm life really looked like in northwest North Dakota generations ago. From milking cows by hand to massive cousin gatherings, to the grit, humor, and family values that shaped their lives — this episode is a living snapshot of rural A...

"This week, Heidi Olson sits down with her husband's Aunt Shirley and cousin Rock to celebrate Caregiver Awareness Month through a journey of family history, resilience, and gratitude. From stories of growing up in a 100-year-old farmhouse without running water to memories of music-filled evenings and multigenerational caregiving, this episode captures the heart of what it means to honor your root...

In this follow-up episode, Heidi Olson and Attorney Valeska Hermanson continue their discussion to uncover the practical side of Medicaid planning — from eligibility traps to timing mistakes that could cost families their farms. They discuss what counts as a gift, why appraisals matter, how to protect assets without disqualifying yourself, and why starting early is the best move you can make. Whet...

In this episode, Heidi Olson sits down with Attorney Valeska Hermanson to break down the basics of Medicaid and long-term care planning—what it is, why it matters, and where to start before a health crisis hits. From essential documents like power of attorney and healthcare directives to common misconceptions about asset protection, Heidi and Valeska share practical steps families can take now to...

In this special Halloween episode of the Pathfinder Legacy Podcast, Heidi Olson and her husband, Kirk, open up about the realities of farming as a couple — from communication breakdowns in the tractor cab to late-night bookkeeping at the kitchen table. They share stories, laughter, and lessons on what it really takes to run both a marriage and a farm together. Whether you're farming side by side o...

When you sell the farm to family at a discount or over time, the paperwork matters more than the handshake. Host Heidi Olsen and attorney Brittany Faust (Neff Law) explain why you should get a real appraisal, file gift tax returns when selling below fair market value, and record/clean up title work so heirs aren't blindsided later. They cover IRS risks (imputed interest/income, penalties), how con...

In this episode of the  Pathfinder Legacy Podcast , host Heidi Olson sits down with attorney Brittany Foust of Neff Law to tackle one of the most complex challenges facing today's farm families — how to transfer land to the next generation without jeopardizing retirement, triggering unnecessary taxes, or losing control. They unpack the differences between a buy-sell agreement and a contract for de...

In this episode of the  Pathfinder Legacy Podcast , Heidi Olson tackles one of the most painful and costly mistakes farm families make—dying without a plan. From real stories of families torn apart by probate battles to simple steps you can take today, Heidi explains why estate planning isn't about death—it's about direction. Learn what happens when you don't have a will, how to protect your land...

In this episode of Pathfinder Legacy, Heidi Olson sits down with Mackenzie Schroeder, who faced the unimaginable—losing both her dad and grandma within one week, neither with a will or estate plan in place. Mackenzie shares her raw experience of stepping up as a personal representative while grieving, the chaos of navigating assets, and the hard lessons she learned along the way. Their conversatio...

In this special mailbag episode of the Pathfinder Legacy Podcast, Heidi Olson tackles real-life scenarios from farm families and business owners. From equalizing heirs to handling sudden debt spikes, Heidi explains what works, what breaks, and how to avoid costly mistakes when it comes to life insurance, trusts, and succession planning. You'll learn how to align your policies with your plan, why l...

Life insurance isn't glamorous—but for farm families, it's the glue that holds everything together when life takes an unexpected turn. In this episode, Heidi Olson breaks down the essentials of policy ownership, beneficiary routing, and the real-world consequences of getting it wrong. Through practical examples and cautionary stories, you'll learn how to ensure life insurance dollars land in the r...

In this special episode of the Pathfinder Legacy podcast, Heidi is joined by Mary Jo Irmen, author of 'Farming Without the Bank,' which shows how farmers and ranchers can utilize the Infinite Banking Concept. Mary Jo is an Authorized IBC Practitioner and has clients in all of the lower 48 states. Tune in as Heidi and Mary Jo discuss cash value financing, real-world policy design, and the need for...

Retirement, succession, and estate planning often fall apart without one critical piece: liquidity. In this episode of the Pathfinder Legacy Podcast, Heidi Olson shares why life insurance is the unsung hero of farm succession. From covering debts and estate costs to keeping acres in the family, life insurance provides the cash families need when they need it most. Heidi walks through real farm sce...

In this episode, Heidi tackles the tough issues surrounding farm and business succession, focusing on a real-life situation from Mike in Eastern South Dakota. At 60, Mike still feels controlled by his 85-year old father despite carrying the farm's financial and operational load. Heidi offers practical advice for others stuck in similar situations, on ownership versus management, acknowledging cont...

In this episode, Heidi explores the critical components of a farm and business succession team, and the importance of vetting each person to make sure their priorities align. Learn about the key roles such as attorneys, accountants, lenders, trust officers, and life insurance agents, and understand the red flags to watch for when selecting your advisors. For guides, checklists, and planning tools...

In today's special episode, Heidi Olson sits down with her daughter, Marv and Ole, who are 5th-generation kids raised on the family farm. They share their unique experiences growing up in a rural community, the valuable skills they've learned, and what it means to be part of a legacy that spans over a hundred years. From showing livestock in 4-H to managing responsibilities on the farm, this episo...

In this episode, Heidi is joined by her husband, Kirk Olson, where they share some stories from their journey along the way. They explore the primary reasons why many farm founders are hesitant, or altogether avoid making plans for succession, and why understanding these top concerns can help in addressing them effectively, ensuring a smoother transition, that alleviates stress and worry for both...

In this episode, Heidi shares some personal experiences growing up on a family ranch, her extensive career in a trust department, and invaluable lessons on succession planning. From stories of miscommunication and family disputes, to moments of reconciliation and understanding, Heidi emphasizes the critical role of clear communication and shared vision in successfully passing on a family farm or b...