How Entrepreneurs Can Become Work Optional with Phil & Trish Calandra

How Entrepreneurs Can Become Work Optional with Phil & Trish Calandra

Author: Lori Harder | YAP Media August 26, 2026 Duration: 54:05
Are you growing your business and making more money, but still wondering if you’re building the wealth and freedom you want? In this episode, Chris and I sit down with Phil and Trish Calandra, CEO and Co-Founder of TruWealth Advisors, to talk about the difference between generating revenue and building long-term wealth. They break down the “revenue trap,” why having multiple financial experts doesn’t always mean you have a unified strategy, and how entrepreneurs can create a clearer path toward their personal wealth freedom number. We also talk about the money stories that can shape your financial decisions, why women entrepreneurs can put their own wealth goals last, and what it means to become work optional. Tune in to learn how you can make your business work toward the freedom you want. Check out our Sponsors: Shopify - Try the ecommerce platform I trust for Glōci. Sign up for your $1/month trial period at http://Shopify.com/happy. Monarch Money -  Get your first year of Monarch Core for half off at http://Monarch.com with code EYH. Northwest Registered Agent - Visit http://northwestregisteredagent.com/EarnFree and start using free resources to build something amazing. Fabric - Join the thousands of parents who trust Fabric to help protect their family. Apply today in just minutes at http://meetfabric.com/earn. Indeed - Indeed is giving Earn Your Happy listeners a $75 SPONSORED JOB CREDIT to help get your job the premium status it deserves. Just go to http://Indeed.com/podcast right now and support our show by saying you heard about Indeed on Earn Your Happy. Momentous - If you want to try Momentous Signature Spec Creatine, head to http://livemomentous.com and use code EARN for up to 35% off your entire first order. Brevo - Meet Brevo…the all-in-one marketing and CRM platform built to help you connect with customers, boost engagement, and grow your business smarter. Get started for free today—or use code HAPPY50 to save 50% on Starter and Standard Plans for the first three months of an annual subscription. Just head to http://www.brevo.com/happy HIGHLIGHTS 00:00 Why making more money doesn’t always mean building more wealth. 02:45 The lesson Phil learned from having just $0.08 in his business account. 06:00 The decision that pushed Trish to take a major career risk and move to Atlanta. 09:45 What is the “revenue trap” and why does it keep entrepreneurs stuck? 15:00 What is your “wealth freedom number”? 22:30 The financial savings that come from having a coordinated strategy. 24:00 Why women entrepreneurs often put their own wealth goals last. 25:30 How time makes compounding work in your favor. 28:15 How your money story influences your financial decisions. 35:00 What should parents teach their kids about money? 38:00 The lesson Phil learned from his grandfather about finding a financial advantage. 40:00 What does it really mean to be “work optional”? 42:45 What financial levers can help you move toward work-optional freedom? 45:15 How the Wealth Creation Scorecard can help you identify financial gaps. 49:30 Can your financial situation be fixed if you’ve made major money mistakes? 53:45 Why the best time to start building wealth is now.  RESOURCES Take the Wealth Creation Scorecard HERE! Find your Wealth Freedom Number HERE! Learn more about the Wealth Ascension System HERE! Learn more about Loop at loriharder.com/loop Get on the waitlist for Mentor Collective Mastermind HERE! Try glōci for 40% off your first order with code HAPPY at checkout - head to getgloci.com FOLLOW Follow me: @loriharder Follow Chris: @chriswharder Follow glōci: @getgloci Follow Trish: @trishcalandra1 Follow Phil: @philcalandra1

Hosted by entrepreneur and author Lori Harder, Earn Your Happy is a raw and relatable look at what it actually takes to build a meaningful life and business. This podcast lives in the messy middle ground between a bold vision and its realization, exploring the risks, the failures, and all those moments of doubt that nobody talks about on a polished highlight reel. Lori’s conversations are grounded in real experience-her own journey as a founder and host-and they cut through the noise of typical business advice. You’ll hear honest stories about the rollercoaster of chasing big goals, where laughter and vulnerability are just as important as strategy. It’s this authentic, no-BS approach that has resonated with so many, earning the show recognition as a top entrepreneurship podcast. Each episode feels like a candid talk with a friend who’s been there, offering not just inspiration but practical perspectives for navigating your own path. Tune in for a dose of reality that’s as motivating as it is genuine, proving that building something you love is never a straight line.
Author: Language: English Episodes: 50

Earn Your Happy
Podcast Episodes
How to Tell Stories That Make People Pay Attention & Buy [not-audio_url] [/not-audio_url]

Duration: 26:05
You could have the perfect offer and still get ignored. In this episode, I’m sharing the (no longer) secret weapon that will grab more attention and make you more money in your business. Storytelling is one of the most v…
From $8K to $100K in 3 Months: How Siff Haider Built Arrae [not-audio_url] [/not-audio_url]

Duration: 1:01:25
Do you have an idea that keeps coming back to you, but you’re still wondering if it’s worth pursuing? In this episode, I sit down with Siffat Haider, co-founder & co-CEO at Arrae. Siff shares how she went from researchin…
How to Get Your Product to Market & Make Sales FASTER [not-audio_url] [/not-audio_url]

Duration: 15:48
How long have you been “working on” an idea that you could have already launched? In this episode, Chris and I talk about why your first launch doesn’t need to be perfect, it just needs to happen. We break down what we l…
How to Make Money From Podcast Guesting (Even on Smaller Shows) [not-audio_url] [/not-audio_url]

Duration: 16:21
What if one of your biggest opportunities to grow your business isn’t another ad, funnel, or social media strategy? In this episode, I’m sharing how podcasting has helped me build authority, create incredible relationshi…
How to Get Back the Habits That Made You Feel Like You [not-audio_url] [/not-audio_url]

Duration: 13:18
Have you ever felt like you’ve lost the thing that used to make you feel like yourself? In today’s episode, Chris and I talk about the things that used to give us energy, creativity, and a mental reset, and how easily th…
How to Move Forward When Failure Feels Like the End [not-audio_url] [/not-audio_url]

Duration: 10:21
Ready is not a feeling, it’s a decision. In this episode, I’m sharing my personal journey through moments of fear, pivots, sleepless nights, and even the times I felt abandoned by God. I’m also sharing how those dark sea…
Get Seen, Get Known & Turn Your Content Into Sales with Angela Simson [not-audio_url] [/not-audio_url]

Duration: 52:50
Are you posting consistently but still struggling to attract the right people into your business? In this episode, I’m joined by Angela Simson to break down how to create content that gets you seen, builds trust, and tur…
How Your Relationship With Time Can Change Your Income [not-audio_url] [/not-audio_url]

Duration: 23:26
Do you ever feel like you don’t have enough time or enough money? In today’s episode, Chris and I break down why your relationship with time and money are more closely connected than you realize. We share examples of how…