EP. 93 | One Lawyer Running Seven Ventures at Once

EP. 96 | Hard Skills Get You the Job. Human Skills Keep It. (w/ Mike Miles)

https://www.linkedin.com/in/mike-j-miles/ [https://www.linkedin.com/in/mike-j-miles/] https://www.milestone-leadership.com/blog [https://www.milestone-leadership.com/blog] Mike Miles spent 20 years at Microsoft. Led teams of 700 people across 11 countries. Helped launch Bing in 75 markets. Held two patents. And nearly burned out trying to take a company public before 9/11 ended that dream. What he walked away with wasn't the stock options. It was a question: is that really the leader I want to be? Today Mike runs Milestone Leadership, coaches executives and impact-focused founders, sits as board chair at Watson Institute, and runs 90-mile events in his spare time. We talk about the Blue Task vs. Red Task framework, how to build the line out your door, why AI is making human skills more valuable than ever, and what 20 years at Microsoft taught him that no business school ever could. Timestamps: 0:00 – Welcome + Mike introduces Milestone Leadership 0:39 – Three things he focuses on: new skills, balance, delegation 1:48 – From IPO to sold for pennies: the pre-Microsoft burnout story 3:54 – The line out your door — the best leadership measure nobody talks about 5:47 – Why coaching leaders wasn't a thing at Microsoft in the early 2000s 6:30 – Hard skills vs. human skills — why we don't value what we can't measure 8:48 – How he works with clients: the 4 assessments (360, DISC, balance, energy) 12:52 – The running question — and why endurance is a leadership lab 13:21 – Stepping outside your comfort zone in another dimension 15:18 – 90 miles in Park City, Utah — and a 100K coming this September 16:48 – Nature, thinking, and what the desert is missing 21:27 – The patent cubes on the shelf — what Microsoft gives you for innovating 22:54 – What gives him the most fulfillment now vs. leading 700 people 26:10 – The Blue Task vs. Red Task framework explained 29:07 – How to delegate, defer, or delete your red tasks 30:44 – The four things you can do with any email: respond, delegate, defer, delete 32:57 – How Mike keeps his workweek under 40 hours on purpose 33:50 – The business manager who's been with him for 25 years 38:30 – Why he blogs without AI — and why that matters 41:55 – Bring Back Blogging — a new hashtag is born 42:57 – What he'd tell his younger self: invest in human skills earlier 45:14 – You can't learn to swim by reading about water 47:15 – The reps that count — and why presence is the rep 49:05 – Running without headphones — and why being alone with yourself is hard 50:06 – Closing thoughts

EP. 95 | You Carried Your Burnout Into Your Business (w/ Candice Van Dertholen)

https://www.linkedin.com/in/candicevandertholen/ [https://www.linkedin.com/in/candicevandertholen/] https://heal.me/candice [https://heal.me/candice] Candice Van Dertholen spent years building other people's businesses — launching a YogaSix studio from four walls and a concept to 400 members, managing Anytime Fitness to 1,500 members, creating communities where people felt at home. Then she burned out. And when she started her own business, she realized she'd carried the exact same energy patterns with her. Today Candice is the founder of The Warrior Within Healing, a speaker, retreat facilitator, and private advisor to conscious business owners. We talk about why most entrepreneurs unknowingly duplicate their burnout in their own companies, what energy work actually is (without the woo), how clarity of self always comes before clarity of strategy, and why the best growth tool she ever used was just being herself in conversations. Timestamps: 0:00 – Welcome + Candice introduces herself and The Warrior Within Healing 0:37 – What a "conscious business owner" actually means 1:20 – Who she works with: high performers leaving high-pressure industries 3:36 – How it started: franchise work, Anytime Fitness, and launching YogaSix 4:37 – From four walls to 400 members — how she built community from scratch 7:12 – Why burnout patterns follow you into your own business 9:29 – How to explain energy work to someone who's brand new to it 10:04 – We all carry energy — and everything we put in our system affects it 12:49 – The boomerang effect: what you give comes back 13:42 – What transformation actually looks like: from burnout to first launch 16:07 – Human Design and how it helps identify where your energy has been displaced 19:00 – The identity crisis moment that comes before real clarity 22:14 – The Jerry Maguire exit — and what really happens in business year one 26:17 – The best visibility strategy: get really good at being you 27:43 – Why AI is pushing everyone back toward in-person connection 29:20 – How she built referral partnerships just by showing up as herself 30:43 – Reputation takes time — put in the reps 31:00 – How to hold space for people at a four-day retreat without burning out 33:12 – In New Hampshire: asked the Divine for guidance before a heavy talk 34:40 – Going back to a contract job in 2024 — and what she learned from it 35:04 – What gives her the most fulfillment 36:20 – Matt's personal takeaway: energy habits follow you from career to career 40:19 – It's a constant evolution — and that's the beauty of it

EP. 94 | The FBI Said He Was on an ISIS Kill List

https://www.linkedin.com/in/tomkirkham/ [https://www.linkedin.com/in/tomkirkham/] https://www.kirkhamirontech.com/ [https://www.kirkhamirontech.com/] Tom Kirkham has been in cybersecurity for 26 years. He's seen everything from bragging rights hackers in the late 90s to an industrial-scale trillion-dollar criminal industry. But nothing changed his perspective quite like the day an FBI agent showed up at his office and told him he was on an ISIS kill list — because a company he signed an NDA with got hacked. Today Tom runs Kirkham IronTech, a managed security services provider ranked in the top 250 MSPs globally for four consecutive years. We talk about how hacking became a $10 trillion industry, why 95% of breaches are caused by human error, how AI is now scaling personalized attacks to target anyone, what ransomware actually looks like from the inside, and why your coffee machine might be your biggest security risk. Timestamps: * 0:00 – Intro: What Kirkham IronTech does * 1:01 – 26 years in IT and security — top 250 MSP globally * 2:06 – Starting the company from a dining room table on January 1, 2000 * 3:02 – When hackers did it for bragging rights — and when that changed * 4:11 – 95% of breaches are caused by human error, not technical exploits * 5:00 – How a ransomware campaign works — the math behind $10M paydays * 5:26 – The FBI showed up and said: you're on an ISIS kill list * 6:19 – How he ended up on the list (a Sun Microsystems NDA got hacked) * 9:14 – Stoicism helped him make peace with it in weeks * 13:31 – The number one threat to every business: ransomware * 14:33 – Hacking is now a $10 trillion industry — third largest GDP on the planet * 16:39 – AI now scales personalized attacks to everyone, not just high-value targets * 17:05 – Matt's real experience: CEO identity stolen, employees sent to buy gift cards * 18:14 – Proactive vs. reactive: how Kirkham operates * 19:07 – Gas pump skimmers, phishing, and cybersecurity beyond the office * 20:17 – Why traditional antivirus (Norton, McAfee) is no longer enough * 22:59 – Chinese cyber warfare and the greatest IP theft in human history * 26:10 – The three pillars: technology, training, governance * 27:28 – Why old laptops are costing you more than new ones * 28:48 – Why Tom replaced every Mac in the company within 6 months of Apple Silicon * 30:22 – They qualify clients as much as clients qualify them * 32:36 – Clients who've been with them 20+ years — and why churn is minimal * 35:29 – From a dining room to a radio show — how he built regional brand awareness * 37:50 – AI in the company: privacy governance comes first * 42:49 – Executive intelligence briefings — what's coming next * 46:55 – What Tom would tell his younger self: trust your gut, embrace failure * 50:17 – MSP 4.0: managed intelligence providers and the AI governance opportunity * 53:09 – Closing thoughts

EP. 93 | One Lawyer Running Seven Ventures at Once

https://www.linkedin.com/in/marcsnyderman/ [https://www.linkedin.com/in/marcsnyderman/] https://npoint.ventures/ [https://npoint.ventures/] At 17, Marc Snyderman and his brother rented a bay at his dad's dealership, made business cards that said "Exotic Care," and started picking up people's cars door-to-door to detail them. He says it would have been a nine-figure exit if he'd kept going. Instead he went to law school, interned at the Philadelphia Stock Exchange, ran operations at a defense contractor from $15M to $60M ARR, burned out, rebuilt, and now runs seven ventures at once — including a subscription-based law firm, a creator marketplace, a lithium-ion fire extinguisher company, and a coffee brand called Teddy Outdoors. We talk about how he flipped the law firm model on its head, what 26% annual growth for five years actually looks like from the inside, how to spot the wrong business partner before it's too late, mental health as a founder, and why vibe coding a full app in a weekend is now completely normal. Timestamps: * 0:34 – Age 17: Exotic Care, door-to-door car detailing, and the nine-figure exit he missed * 2:23 – "That would 100% be a nine-figure exit today" * 3:41 – How he ended up in law: a Hansel and Gretel mock trial in second grade * 4:09 – Paying his way through law school from day one * 4:48 – Interning at the Philadelphia Stock Exchange * 5:06 – From corporate lawyer to COO — and 10 years running a defense company * 5:58 – 26% annual growth for five straight years — what actually drove it * 7:19 – Would he need fewer people today with AI? His honest answer * 8:02 – Excel didn't kill accountants — and AI won't kill lawyers * 10:17 – Legal as a Service (LaaS): flipping the billable hour model upside down * 12:14 – Are other law firms copying the subscription model? * 13:32 – ChatGPT hallucinated a case citation — a lawyer got disbarred * 14:48 – The private AI tools built specifically for lawyers * 16:00 – Next Point Ventures: the airport analogy * 17:03 – The only thesis: "We don't work with assholes" * 17:22 – Ukreate: a creator marketplace for travel brands and hotels * 18:58 – VendOnBoard: vendor compliance automation * 19:55 – The lithium-ion fire extinguisher — why your regular one won't work * 22:13 – Teddy Outdoors coffee: step outside, put the phone down * 23:46 – Performance coffee with mushrooms — trying to make it taste like coffee * 24:34 – Matt's Milton Hershey story and the Switzerland recipe * 25:40 – Entrepreneurial ADHD: open, focus, move — one window at a time * 26:37 – Vibe coding a full app with audit capability in a weekend * 28:11 – How to spot the wrong business partner before it's too late * 29:26 – Business divorces: the ugly reality of startup partnerships * 30:05 – The Warren Buffett / Charlie Munger restaurant test for CEOs * 31:47 – Matt's never held a real pager * 32:05 – Health, burnout, depression, and the semicolon tattoo * 33:41 – What Marc would tell his 17-year-old self * 35:03 – Why failure has one root cause, but success has 100 * 36:53 – Neuroplasticity, individuation, and why talking to younger people is mission critical * 37:58 – When we all became uncomfortable with our own thoughts * 40:32 – What gives Marc the most fulfillment

EP. 92 | This AI Answers Your Phone at 3AM and Books the Job — CallTex Co-Founder

Connect with Casey: LinkedIn: https://www.linkedin.com/in/casey-purington-537103ab/ [https://www.linkedin.com/in/casey-purington-537103ab/] Website: https://www.usecalltex.com/ [https://www.usecalltex.com/] Casey Purington has spent 15 years obsessing over one thing: what happens when a customer calls a home service company. Most of the time — especially after hours — nothing good happens. The phone rings. No one answers. The customer calls the next company on the list. And the HVAC company just wasted $300 in marketing to get that call. Casey built CallTex to fix that. An AI voice agent that answers in under a second, pulls the customer's history from Service Titan, quotes the right price, books the job, and logs everything — without a single human involved. We talk about how AI voice agents actually work behind the scenes, why transparency with callers matters, how Casey cold calls companies at midnight to prove his point, his plan to land private equity groups, and why he's betting everything on AI. Timestamps: 0:00 – Welcome + Casey introduces himself and CallTex 0:55 – From the car business to call centers at 18 2:30 – His first day in a contact center: a chair, a headset, and a notepad 3:40 – What great call handling actually looks like — and why most companies miss it 6:04 – How AI pulled him out of consulting and into building 7:00 – Three buckets: inbound, outbound, and proactive follow-up 8:00 – Happy check calls, tune-up campaigns, and the CRM integration 9:55 – Playbooks, tagging, and how the back end works 11:16 – Who's adopting AI fast — and who's still talking about it 13:39 – The Yellow Pages moment: early adopters win, resisters get left behind 14:36 – Should you disclose the caller is talking to AI? 17:00 – Transparency, hallucination, and the hybrid approach 20:09 – What happens to the call center agents he trained? His honest answer. 22:09 – The full customer journey with CallTex — demo to live 24:47 – Tagging, routing, knowledge base, and advertisement integration 27:12 – This is not an answering service — what makes CallTex different 29:23 – Onboarding takes days, not weeks — but you need one owner 30:18 – Why every home service company needs a call center manager 32:38 – Can the manager role be remote? Yes — and Casey plans to offer it 36:01 – How they find customers: calling companies at midnight 37:00 – The leakage report: Casey records missed calls and sends them to the owner 39:27 – The private equity play — scaling dozens of locations at once 41:00 – "We couldn't get the big players to do what you did" — a client this week 43:22 – Where is AI voice going over the next decade? 45:28 – Why off-the-shelf AI won't cut it — the builders vs. the plug-and-play crowd 48:19 – Matt's take: AI is the direction, human in the loop stays 49:46 – Closing thoughts