by Matt Dery
Andrew Blake grew up on Blake Farms, a third generation apple orchard outside Detroit. He came back from college with one good idea after a few bad ones and built a business plan around hard cider. The family business ran on a brutal cycle. Eighty percent of the revenue came in two months. They'd balloon up to 500 seasonal employees and then spend the rest of the year bleeding cash. It made every decision feel like a gamble. He pitched his dad and uncle on hard cider right out of college. That bet became Blake's Beverage Co, now the second largest hard cider company in America, with plants in New York, Michigan, and Oregon. Along the way he learned what it costs to scale on cheap debt, what it takes to bring outside executives into a business your family has always run, and how to know when you're the founder and not the operator. → Turning a college recipe into a national cider company → Bringing outside executives into a three-generation family business → Why he calls himself a founder, not an operator → Lessons from scaling on cheap capital and three new plants → Building an AI underwriting startup from scratch → Staying aligned with his wife while running multiple businesses He's founded or co-founded six companies and he still says the hardest part was figuring out what he's actually good at, then getting out of the way and letting other people do the rest. Thanks to Andrew for making the time to sit down and be this honest about it. Chapters 0:00 Intro 1:48 Growing up on Blake Farms 2:36 The bad ideas before the good one 5:23 Fixing an 80% seasonal business 7:53 Making memories is always in season 9:41 Fifteen years of professionalizing the family business 16:07 Founder vs. operator, and staying grounded 22:15 Marriage, kids, and staying aligned 25:14 Building Alloan, the AI underwriting startup 31:05 Cheap capital, three plants, and what it actually takes ~~~ This episode is powered by Freedom-First Pathway. Ready to take back control of what you’ve built? https://www.ffpathway.com
Freedom-First Pathway’s guest in this episode put in eighty to a hundred hours a week for his dad, and never saw a dime of overtime for it. Let’s meet Najeeb Haddad, he’s the president and CEO of ENDOCORP. His dad started the company in 1996 sourcing and repairing parts for endoscopes. Najeeb grew up in that shop before he ever sat behind the desk. ENDOCORP now touches 4M patients a year through the parts it puts back into circulation, with a plan to hit 10M by 2030. What this episode covered: → Taking over the family business and earning trust from people who watched him grow up → Running the entire company with one other person during Covid → Building a culture where employees vote on who's actually living the values → Learning to let go of control and step out of his own meetings → The five year plan to serve ten million patients a year Thanks to Najeeb for making the drive to Southfield to sit down for this one. Chapters 00:00 Intro 02:30 Meet Najeeb Haddad and the ENDOCORP story 05:00 Second generation, eighty hour weeks, and the owner's son problem 10:30 What ENDOCORP actually does in endoscopy repair 12:58 Getting buy in, small wins, and building a culture that fits 18:00 Giving up control and stepping out of his own meetings 20:00 Consolidation in the industry and staying close to customers 21:30 People are the biggest asset and the biggest risk 23:30 Running the company alone with his brother-in-law during Covid 26:00 The five year plan to serve ten million patients ~~~ This episode is powered by Freedom-First Pathway. Ready to take back control of what you’ve built? https://www.ffpathway.com
Ivan Katz started Great Lakes Landscape Design in 1989 with no job, no plan, and a few months of backpacking through Europe behind him. 37 years later he runs sixty employees as the Visionary of the organization. Even during Covid, the company saw great growth, up until a slump last year. Ivan didn't fix it by working harder…. He brought in EOS and started handing pieces of the business to people who could do them better than he could. And slowly, the company stopped needing him to run everything. In this episode of The Freedom-First Pathway Podcast, they covered: → Starting a landscaping company with no experience and no money → Why 71% of the business comes from repeat clients → Learning to let go of sales after almost 40 years of owning it → Getting through a Michigan winter of Covid restrictions Thanks to Ivan for making the time between job sites to sit down and talk through all of it. Chapters 00:00 Intro 01:59 From backpacking through Europe to starting a landscape company 05:39 What actually sets Great Lakes apart from competitors 07:55 The brand promise: we make it right, no matter the cost 09:15 Becoming the visionary and learning he's a 30% guy 11:48 Letting go of sales and breaking the machine 14:20 Building a mission around transforming employees' lives 17:41 From cutting grass himself to building career paths for the team 20:28 Reading the market in 2026 after a rare downturn 24:18 Ten years out, Covid lessons, and protecting the reputation ~~~ This episode is powered by Freedom-First Pathway. Ready to take back control of what you’ve built? https://www.ffpathway.com
Carla Marsh runs Accurate Pay Systems, a payroll and HR company out of Sterling Heights, Michigan. She's been on payroll since her second job out of college, and she built a company around fixing the problems other providers leave behind. She wasn't a CPA, so it took a year and a half and a letter from her own accountant just to get the IRS credentials to process payroll herself. Based on that grit alone, she's built an all-female team of eight, spread across three states, with a Google Meet every morning and a wine tasting on the calendar too. And she still shows up to CPA firms with donuts, because that's what built her client base in the first place. Here’s what Matt and Carla covered on this episode: → Why business owners get blindsided by unemployment and tax notices → Buying out a business partner and learning payroll operations from scratch → Getting called out by her own staff, and changing because of it → How pay-as-you-go workers comp actually works → Running an all-female team across three time zones Thank you to Carla for making the time to sit down and tell this story. We appreciate you coming and sharing your time! Chapters 00:00 Welcome and meet Carla Marsh, the "Payroll Wizard" 02:19 The payroll mistakes that blindside small business owners 02:48 Three business partners, one buyout, and learning payroll from scratch 07:37 The staff pushback that changed how she leads 11:12 Pay-as-you-go workers comp, explained 12:58 An all-female team spread across three states 16:06 Where AI fits and where it doesn't 17:19 The campground kid who became the "number two" sales rep who failed 17:59 Donuts, coffee, and the CPA strategy that built the business 21:22 What's next for Accurate Pay Systems ~~~ This episode is powered by Freedom-First Pathway. Ready to take back control of what you’ve built? https://www.ffpathway.com
Most family businesses don't survive the second generation. Dan Beaudoin is the owner of DMF Bait Company, a live bait operation his father and uncle launched in 1977 out of Waterford, Michigan. They were school teachers who needed summer income and stumbled into a pyramid scheme. They lost their life savings but pivoted to nightcrawlers and built something nobody saw coming… DMF is now in 49 states: Walmart, Cabela's, Bass Pro, and expanding into convenience stores. Plus, Dan's son just started full time; generation three is being planned intentionally, the way Dan wishes his own transition had been. In this episode, Matt and Dan covered: → Why most family business successions fall apart before they even start → How Dan navigated the tension between honoring his father's legacy and growing past it → What it looked like to push for a bigger vision when everyone told him he was too young and too wrong → How EOS and Vistage changed how Dan leads today → What he's watching right now: supply chain pressure, expansion costs, and keeping his team together Dan, thank you for coming on the show and sharing your story with our audience! Chapters 0:00 - Welcome to the Freedom First Pathway Podcast 0:44 - Introducing Dan Beaudoin and DMF Bait Company 1:37 - How a Pyramid Scheme Started a Worm Business 3:31 - From Nightcrawlers to Kmart: The First Big Break 5:30 - Growing Up in the Business and Joining Full Time 6:31 - The Succession That Had No Plan 8:17 - Getting Legal Counsel and Making It Work 11:29 - Honoring the Past While Changing the Future 13:25 - The Las Vegas Breakfast That Changed Everything 16:38 - How DMF Gets Worms to 49 States (and Where to Buy Them) 18:17 - How Dan Operates Today: Culture, EOS, and His Son's Future 20:05 - Blind Spots and What He's Still Learning as a Leader 21:14 - Supply Chain Costs and What Business Owners Are Facing Right Now 27:59 - Culture, Core Values, and Having Fun With Worms 28:53 - Closing Thoughts ~~~ This episode is powered by Freedom-First Pathway. Ready to take back control of what you’ve built? https://www.ffpathway.com
Andrew Agbay started Decypher out of frustration. For the next 26 years, he ran it ALONE: All new business came through him. Finances and Operations flowed through him. The company grew. But so did its weight. About a year ago, Andrew hit a wall. He saw that if something were to happen to him 26 years of work could disappear. So he made a call most founders resist… He let go; he brought in a bookkeeper, a salesperson, an operations manager. He opened the books to his team. He stopped being the answer to every question. And what happened surprised him. Here are the things he and Matt talked about: → How sharing financials created an ownership mentality across his whole team → What the EOS framework actually looked like in practice at a 10-person company → How AI has let Decypher cut project costs by up to 80% and reach clients they couldn't price before → Why Andrew's hardest leadership lesson was realizing the problem was himself → What founders get wrong about trusting their people Andrew said the more you reduce dependency on yourself, the more you're actually protecting what you built. Thank you Andrew for coming on and sharing the lessons, struggles and wins! Chapters 0:00 - Welcome and Introduction 0:38 - Andrew Agbay and the Story Behind Decypher 1:07 - How Decypher Automates Data and Builds Custom Solutions 3:39 - Where the Name "Decypher" Came From 4:38 - 27 Years In: What Andrew's Ownership Journey Has Really Looked Like 5:43 - Implementing EOS and Building a Leadership Team for the First Time 7:29 - Blind Spots: What Andrew Couldn't See When He Was Running Everything 8:31 - Encountering AI and Leaning on His Team When He Didn't Have the Answers 10:16 - On Letting Go: Trust, Control, and Sharing the Financial Picture 12:07 - Ego Checks and the Paradigm Shift of Distributed Leadership 16:33 - How AI Is Changing Decypher's Pricing Model and Client Reach 18:39 - Who Decypher's Sweet Spot Client Is Today 22:06 - What's Next: The Sibyl AI Platform and the Road Ahead 24:10 - Advice for Founders on AI and Reducing Owner Dependency 26:17 - Family, Kids, and the Season of Life Andrew Is In Right Now 27:28 - Closing Thoughts and Outro ~~~ This episode is powered by Freedom-First Pathway. Ready to take back control of what you’ve built? https://www.ffpathway.com
Jacqueline Kaltz-Coulombe grew up in construction. Her family's company, the job sites, the contracts, the sleepless nights around the dinner table. She began Kaltz Coulombe Law as a boutique construction and corporate firm, but it evolved into something closer to an advisory partnership: Fixed pricing. Membership models. Real relationships. Which is why she’s now the Chief Owner Strategist of Freedom-First Pathway. In this episode of The Freedom-First Pathway Podcast, she and Matt cover: → What it costs owners when most advisory relationships stay transactional → How the Pathway Assessment creates a full picture that no single advisor can see → What "growth strategy" means when you strip away the buzzword → Why construction business owners carry a kind of pressure that most advisors miss → How family dynamics show up inside companies Owners feel alone. You can have a great CPA, a solid financial advisor, and a sharp attorney and still feel like you're piecing it all together yourself. That’s why we give owners a team that actually communicates. Jacqueline, thanks for being a guest on the episode - we appreciate your insight so much! Chapters 0:00 - Introducing Jacqueline Kaltz-Coulombe 1:40 - Growing Up in Construction and Finding a Gap in the Market 3:25 - Why Big Law Left Owners Without a Real Partner 5:10 - What Brought Jacqueline to Freedom First Pathway 6:55 - Why Integration Has Been Missing From Advisory for So Long 8:00 - How the FFP Assessment Process Works 9:25 - Do Existing Advisors Push Back? 10:40 - What Gets Jacqueline Excited About This Work 11:45 - The Biggest Challenge of Running Her Own Firm 13:15 - "Growth Strategy" and What It Actually Takes to Execute 16:00 - Construction Business Owners and the Weight of Wearing Every Hat 18:30 - How Legal Work Opens the Door to Deeper Conversations 21:05 - Working In the Business vs. On the Business 23:20 - The Biggest Problem Jacqueline Sees Right Now 24:05 - Final Takeaway: If You Want More, We're Here ~~~ This episode is powered by Freedom-First Pathway. Ready to take back control of what you’ve built? https://www.ffpathway.com
Most business owners have a great team around them: A CPA. An attorney. A wealth manager. Maybe even an exit planner. But why do things still feel fragmented? That's the gap Chris Cousins has spent 30 years trying to close. Chris is the co-founder and President of Freedom-First Pathway, a company built around one uncomfortable truth: the advice industry is siloed by design, and owners are paying the price. Not just financially. In their leadership. In their families. In what happens to them when the business they've built becomes the only thing they are. The stories he shared hit close to home. Owners who sold their company and found themselves in the regret statistics three years later. Founders who bought a $250,000 Porsche they never wanted because something had to fill the space the business left behind. High-performing men and women driving the U.S. economy, running on cognitive overload, unable to see the blind spots their own behavior was creating. Chris and Matt covered: → Why fragmentation between advisors leads to worse outcomes, even with a great team → How cognitive overload shows up in owner behavior before anyone notices → What the behavioral neuroscience piece actually means (and why it's not therapy) → The real reason owner regret after a sale is so common → Why integrating your personal vision with your business vision isn't extra work — it's the work Most owners are running toward something and away from something at the same time, and they don't know which one is driving the bus. That's where everything starts to break down. Chapters 0:00 - Teaser 0:45 - Introducing Chris Cousins, Co-Founder of Freedom-First Pathway 1:24 - What Is Freedom-First Pathway and Why Does It Exist? 3:01 - The Silo Problem: Why Advisors Don't Talk to Each Other 4:44 - Exit Planning's Progress and What's Still Missing 5:43 - How the FFP Team Came Together 8:25 - The Pathway Assessment: How the Process Works 11:34 - Business Owners as Heroes: Who FFP Is Really Built For 15:10 - When the Business Becomes Your Identity 16:40 - Behavioral Neuroscience: Not Therapy, Something Deeper 18:25 - Early Warning Signs of Founder Misalignment 20:06 - "I Just Need Growth Right Now": Handling the Most Common Objection 22:09 - What Chris Has Learned as a Business Owner Himself 24:35 - What Success Looks Like at the End of the FFP Process 27:03 - Final Thoughts and What's Coming Next A HUGE thank you to Chris for being the first guest ever on the Freedom-First Pathway podcast! ~~~ This episode brought to you by Freedom-First Pathway https://ffpathway.com/