Chief Milestones
Chief Milestones is a business podcast exploring how founders and parents build meaningful companies without sacrificing their health, families, or values.
Through honest conversations with entrepreneurs, investors, parents, and next-generation leaders, the show dives into the real milestones that shape business, wellness, and life.
New episodes release Tuesdays and Fridays.
Episodes
84 episodes
The Renovation Is Chaos And So Are We | Katie Nelsen | Part 5
A week where they barely spoke, an RSV outbreak handled solo, and the annual ritual that keeps them aligned anyway.In Part 5, Katie Nelsen talks candidly about what it takes to stay a team with her husband while raising three k...
Fevers, Vaccines & Judgment - The Social Cost of Doing It Differently | Katie Nelsen | Part 4
"You think you're better than me" - the reaction Katie Nelsen gets most when people find out how her family eats.In Part 4, Katie talks about the social cost of raising kids on a different diet than everyone around them: the as...
You Can Feed Your Family Well Even On The Busiest Days | Katie Nelsen | Part 3
They ran out of pancake mix one night and panicked - then realized they didn't need it at all.In Part 3, Katie Nelsen gets into the daily mechanics of running a "clean eating" household with three young kids: how meal planning works without...
Cracking the Cough: An Elimination-Diet Story With Katie Nelsen | Part 2
A cough that lasted for weeks, an answer that wasn't good enough, and a two-year process of figuring out why.Katie Nelsen talks through how her oldest daughter's unexplained nightly coughing led her down an elimination process ...
From Flips To Rentals: Strategies That Survive Any Market | Robert Speckert | Part 1
This episode isn't about real estate cycles. It's about the pivot he didn't choose, and the deal structure he built because a client had a nightmare.Robert Speckert has been investing since 2004 and agenting since 2019 - 45+ un...
The 'Family Vacation' That Was Actually a Secret Scouting Trip (Real Estate Mom Tells All) | Katie Nelsen | Part 1
Katie Nelsen didn't know the family vacation her husband Luke planned was actually a scouting trip - he'd been quietly researching Tennessee's Smoky Mountains while commuting three hours to work each week with a newborn at home. That trip be...
The NOI Math Behind 3 Hotel Deals in 6 Months | Harshad Lalan | Part 5
Harshad Lalan bought three boutique hotels in six months - not according to plan, but because the opportunities and partnerships lined up. In Part 5, he breaks down the real reason he moved from short-term rentals into hotels: value-add reno...
Decision Fatigue, Masterminds, and 3 Hotels in 6 Months | Harshad Lalan | Part 4
Harshad Lalan has outsourced almost every daily decision - a remote trainer runs his workouts over WhatsApp, a chef plans and preps every meal, an AI calendar tool reschedules his tasks automatically. The reasoning: decision fatigue is real,...
Dividing a Business (and a Marriage) Without a Fight | Harshad Lalan | Part 3
Harshad Lalan admits the mistake outright: when he hired the first executive assistant for his wife Ishita, he unknowingly built the job description around what he'd want in an EA, not what she needed. In Part 3, he breaks down how that fail...
Building Systems That Scale Without Chaos - VAs, AI Messaging & Letting Go of Control | Harshad Lalan | Part 2
Harshad Lalan built his STR systems the way he was trained to build airplane systems - checklists, redundancy, everything documented. In Part 2, he breaks down the four-person team structure (one thinker, three doers) that lets him step away...
How He Decides What's Worth His Time - Growth, Refining & the Sedona Bet | Harshad Lalan | Part 1
Growth is exciting. Refining is what pays the bills. In Part 1, short-term rental and boutique hotel operator Harshad Lalan walks through the three-filter system he uses before taking on any new property - excitement, ROI, and long-term fit,...
Inside the World of Arangetram: Cost, Readiness, and the Debut She Refused to Compromise"| Prabha Nair | Part 3
This episode is about the client request she turned down - and what it cost her.Prabha Nair has trained Bharatanatyam students for eight-plus years at a stretch, building toward a debut performance called an Arangetrum. In Part...
Teaching Bharatanatyam Across Faith, Gender, and a Student Who Walked Away | Prabha Nair | Part 2
This episode is about what it costs to hold a 2,000-year-old art form to one standard - regardless of who's learning it, where they were born, or what would be easier to teach instead.In Part 2 of this conversation, Prabha Nair...
Building A Dance School On Word Of Mouth | Prabha Nair | Part 1
This episode is about what it takes to run a 25-year-old studio without ever spending on marketing, without chasing enrollment, and without softening a discipline standard to keep paying students.In Part 1 of this conversation,...
What I Found After Everyone Left | Lynn Schwarber | Part 5
Her kids left for college and her marriage ended in the same year - and she says it was, in a strange way, the right time for both.In Part 5, Lynn Schwarber - top-producing realtor - talks candidly about the mourning peri...
Diabetes Remission Starts With Daily Choices | Dr. Prasanthi | Part 4
This episode is where the biggest blood sugar myths get taken apart directly. In Part 4 - the final part of this conversation - Dr. Prasanthi breaks down why keto may work against insulin resistance long-term, whether diet-alone dia...
You Can Still Get Rich In Real Estate If You Start Now | Lynn Schwarber | Part 4
In Part 4, Lynn Schwarber - top-producing realtor and mom of four - breaks down the actual mechanics of client retention, how she ran her business around triplets' sports schedules, and what she tells people who think they don't have time or...
How A Busy Realtor Rebuilt Health And Happiness Without Quitting | Lynn Schwarber | Part 3
In Part 3, Lynn Schwarber - top-producing realtor and mom of four - talks candidly about burnout at the height of her career, the negotiation approach that actually wins deals, and what she learned about herself after her divorce....
Fear Is The Real Wealth Killer | Lynn Schwarber | Part 2
This episode is about a $2,000 gap, a couple in tears, and a negotiation made with the seller still sitting at the table.In Part 2 of this conversation, Lynn Schwarber - agent with Comey & Shepherd and investor in long-term...
Triplets, a Crash, and a $50k First Deal | Lynn Schwarber | Part 1
This episode isn't about real estate advice. It's about what it takes to start a commission-only career the year after the housing market collapsed.In Part 1 of this conversation, Lynn Schwarber - agent with Comey &...
How To Lose 70 Grand And Keep Going | Dylan Koch | Part 5
This episode is about the deal he says he'd never do again.In Part 5 - the final episode of this conversation - Dylan Koch, off-market real estate investor and operator in Cincinnati, breaks down what happens when the underwrit...
Muscle, Glucose, and the Real Case for Plant-Forward Eating - What Actually Moves the Needle on Insulin Resistance | Dr. Prasanthi | Part 3
This episode is about the actual mechanism behind insulin resistance - and why most advice skips it. In Part 3 of this conversation, Dr. Prasanthi breaks down how muscle mass drives glucose absorption, what real plant-based nutrition require...
How To Find Off Market Real Estate Deals And Fund Them Smart | Dylan Koch | Part 4
This episode isn't about finding the perfect deal. It's about knowing which assets you're building for income - and which ones you're holding for life.In Part 4 of this conversation, Dylan Koch - wholesaler, buy-and-ho...
How To Buy Small Multifamily With Seller Financing And Sleep At Night | Dylan Koch | Part 3
This episode isn't about finding good deals. It's about what it actually takes to structure them, follow up long enough to close them, and build a system that works when the market doesn't.In Part 3 of this conversatio...
Building An Authentic Personal Brand As A Working Mom Creator | Suhashini Nathan | Part 2
In Part 2 of this conversation, Suha gets into the decisions she's made as a creator that most people don't talk about - which metrics she actually tracks, why she stopped planning her posts so carefully, how she handled her first negative c...