Live Your Legacy w/Tanner O’Brien

About Live Your Legacy w/Tanner O’Brien

The Ownership Advantage™ is the go-to podcast for business owners and entrepreneurs who want to move beyond just making money and start building lasting wealth. Hosted by Tanner O’Brien, this show breaks down the strategies, systems, and mindset shifts required to transform your business from an income source into a true asset - one that works for you, not the other way around. Each episode dives into practical insights on scaling, exiting, and reinvesting profits to create generational wealth. Whether you’re looking to remove yourself from daily operations, increase your business’s valuation, or start acquiring assets beyond your company, this is where you get the real playbook. Welcome to The Ownership Advantage - where business isn’t just a job, it’s your greatest wealth-building tool.

Publisher

Tanner O’Brien

Category

business

Language

en

Explicit

No

First episode

6 Aug 2023

Latest episode

21 Oct 2026

Latest episodes

180 episodes in the feed.

1. 

   21 Oct 2026

   Stop Saying "I'm Busy." Here's What to Say Instead.

   Someone asks how you’re doing, and before you even think, it comes out: ”Busy.” I say it all the time. And it’s true. I’m running multiple businesses, raising two kids with my wife, writing, speaking, traveling and building new things. But here’s what’s been hitting me lately: I asked for almost all of it. So is ”busy” really how I want to describe my life? In this episode I talk about the story we tell ourselves about being busy, why so many entrepreneurs wear busyness as a status symbol, and why a business where everyone needs you might not be a great business at all. It might just be a demanding job that pays you less. Plus a simple one-week experiment you can start today. In this episode: - Why the words we use start to shape how we experience our lives - The difference between describing your life and defining it - The entrepreneur trap: busyness as a status symbol - What ownership really means: not the absence of work, but more choice over the work - The one-week ”How are you?” experiment - When ”too busy” is a real signal that something needs to change Chapters: 0:00 ”Busy.” My automatic answer 0:25 Everything that’s going on 0:55 I asked for this 1:29 A different answer: ”Amazing!” 2:13 Nothing changed except the story 2:31 This isn’t positive thinking 3:12 The things we say all the time 4:05 I want more of the right things 4:28 A quick word from ActionCOACH 5:12 The entrepreneur trap: busy as a status symbol 5:50 A business, or a demanding job? 6:33 What ownership really means 6:41 The one-week experiment 7:29 If you’re too busy, maybe you are 7:58 Building the life you wanted Get your free 2-week business diagnostic from ActionCOACH Benefic Group: https://actioncoachbeneficgroup.com/diagnostic Get my new book, The Ownership Advantage: https://tannerobrien.com/book I’m Tanner O’Brien, CEO of ActionCOACH Benefic Group, founder of Benefic Marketing and author of The Ownership Advantage. Thanks for being a part of my world. Let’s go build some amazing things together.

2. 

   14 Oct 2026

   If You Sit on a Nonprofit Board, You're Liable for It

   Jodee O’Brien has spent more than 35 years in the nonprofit sector, including CEO roles at two different United Ways. She now runs the nonprofit practice inside our coaching firm, and she built something called the Mission Continuity Framework out of the pattern she kept walking into. She is also my mother, which made this episode more fun than most. She’s usually brought in as the fixer. One Main Street organization had zero dollars and zero board support when she arrived. A United Way was down to four board members and almost no staff. What she found in both was the same thing she finds nearly everywhere, which is that the mission is usually fine and the back office is where things fall apart. The line from this conversation that matters most to anyone in business: if you sit on a nonprofit board, you are liable for that organization, whether you realize it or not, from the moment you sign. Plenty of people take a board seat because it looks good on a resume. That’s the wrong reason, and it carries real exposure. We spent a while on transitions, because that’s where organizations break. Boards turn over every year or two and burn out, because board members have real jobs. Directors leave without warning, or get let go, and the board discovers it has no plan and two people left in the office. When a founder or long-tenured director has been running everything out of their head, there’s nothing written down to hand over. Programs stall, communication to donors goes silent, and money stops arriving at exactly the moment the organization can least afford it. Her fix starts with structure most nonprofits never build. A board matrix, so you know what expertise you have and what’s missing, whether that’s an attorney, a finance person, or a fundraiser. A board succession plan, not just a staff one. Real onboarding and training for new board members. And a written transition plan that assigns responsibilities to roles rather than to people, so it holds no matter who’s in the seat. Then we got into the Nonprofit Organizational Health Review itself. She scours documents against a 230-point checklist, interviews every board member, key staffer, and stakeholder, and will go talk to former employees when there’s something that needs digging out. Everything gets graded red, yellow, or green across five areas including governance and fundraising. Most organizations show a lot of yellow and red at first, often because nobody can find the documentation rather than because it doesn’t exist. The output is a roadmap with timelines, sorted by what’s critical. One organization came in almost entirely red. They’re greens and yellows now, and some of those yellows stay yellow on purpose, because policies need annual review and that’s a feature rather than a failure. A board member who’d been certain the organization was finished told her afterward that they weren’t as bad as they thought. There’s a story in here worth staying for. Running RAGBRAI, the Register’s Annual Great Bicycle Ride Across Iowa, through Mason City meant coordinating 32 separate volunteer committees, city government, police, fire, and 35,000 visitors. The police committee named themselves the Just Wanna Have Fun committee. The organization came out of it stable with a cushion for the first time. Her closing ask is free and anyone can do it. If you’re not involved in something that gives back, find something that matches your passion and the time you actually have, because these organizations need business-minded leaders on their boards. And if you are already on a board, start asking the hard questions at the next meeting. Do we have a succession plan? When was our last strategic planning session? Did we follow it? Then watch whether the questions get answered.

3. 

   7 Oct 2026

   The 4 Freedoms: A Day You'd Actually Want to Repeat

   Somebody once said that happiness is repeating a day you love as many times as possible, and I have not been able to shake it. Partly because it’s a good line, mostly because almost none of the business owners I coach have a day they love. They have a day they survive. Back to back meetings, fires, obligations, and a running promise to themselves that the freedom part starts after the next milestone, the next revenue number, the next hire. Someday doesn’t come. Not because people are lazy, but because someday has no definition. Ask an owner what freedom actually looks like and you’ll usually get a feeling rather than a picture. Nothing specific, nothing they could measure, no way to tell whether the last twelve months moved them toward it or away from it. That’s how you end up permanently chasing something you can’t catch. A repeatable day, for me, is one whose structure holds no matter where I am. Neighborhood, beach, new city, doesn’t matter. That’s not retiring to do nothing forever, which sounds boring and purposeless. It’s a mix of creation and rest, building and being, contributing and recharging, with room to take care of my mind, my body, my family, and the work. The framework I use for defining it is four freedoms. Time freedom is control over the calendar. Not having no obligations, which is unrealistic and dull, but choosing them. Mine is a core work window of ten to four on the days I work, under eight hours a week on business operations by the end of the year, light or empty Fridays, and a morning routine nobody is allowed to interrupt. Financial freedom is runway that removes fear. Not never thinking about money, which is a fantasy, but money not being the thing driving the decision. Reserves funded at six months or more of operating expenses and personal runway, experiences paid for without debt or guilt, discretionary spending that doesn’t need a justification, and cash flow that clears living expenses every month with margin. Family freedom is being present for the things that matter. Not never working while the kids are awake, which isn’t realistic if you’re building something, but not letting work eat the moments that count. Home by five most days. Phone away at dinner, not face down on the table, actually away. At the kids’ activities. Real time with my wife rather than coexisting in the same house. Health freedom is having the energy to enjoy what you built. You can have all the time and money in the world and none of it matters if you’re exhausted and in pain. Mine is measurable on purpose: resting heart rate under fifty, strength benchmarks I check quarterly, seven or more hours of sleep six nights a week, blood work in optimal ranges rather than merely normal, and a daily one to ten score on whether my energy at four in the afternoon still matches my energy at nine in the morning. Your numbers should look different from mine. That’s the point. What matters is that you have numbers, because a goal is binary. You hit it or you miss it, and missing feels like failure. A benchmark you track gives you progress to point at, which means you get to feel some fulfillment on the way rather than only at the end. All of it comes back to something I was reminded of about six years ago. Business is the vehicle for the life you want. It was never supposed to be the outcome. The Ownership Advantage releases September 25, 2026. More at tannerobrien.com/book

Who has been a guest on Live Your Legacy w/Tanner O’Brien

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

• Kyle Bailey
• Brad Barber
• Bart Davis
• Dave Wolcott
• Justin Dixon

Reach and audience

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Apple Podcasts (US)

5.0 / 5

1 ratings

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Books guests

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