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Self-Employment Success Podcast
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Self-Employment Success Podcast

Author: Leland Gross CFP®

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This is a podcast about success for self-employed business owners who want to break through to the next level in their business and have a life in the process. We'll go behind the scenes with CERTIFIED FINANCIAL PLANNER™ and small business owner Leland Gross to hear stories of other how other self-employed business owners navigated the inevitable challenges that arise on the path to success. And get insight from leading business consultants on how to break through to the next level in your business. Whether you own your own small business and want a community of like-minded people who can celebrate and commiserate with you, or you are thinking about making the leap into entrepreneurship, this podcast is for you!
52 Episodes
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Welcome to What Works Wednesday. Today, we're exploring health savings accounts (HSAs)—what they are, why they're important, how to qualify, and how to maximize their benefits. HSAs are powerful yet underutilized tools that offer triple tax advantages: tax-deductible contributions, tax-deferred growth, and tax-free withdrawals for medical expenses. Let's dive into how to make the most of your HSA.
My guest on today’s podcast is Hannah Johnson. Hannah is the founder of Delightful Deliveries, a business providing personalized pop-by services to businesses trying to stay top of mind with their clients, prospects, and referral partners. In this episode Hannah shares her journey of Self-Employment. She started by helping her husband create and deliver pop-by’s and in doing so found that other services over charge to just drop off raw supplies that you then had to assemble and deliver yourse...
Welcome to What Works Wednesday! Today, we're tackling a common question: what to do with that old 401k or 403b from a previous job? Job-hopping is common, but managing old retirement accounts can be tricky. Join me as we explore your options and make the most of your savings. Let's dive in!
My guest on today’s podcast is Heather Fischer. Heather is a life and leadership coach and the founder of MTL Coaching. Heather helps individuals and couples foster growth and purpose in their life through helping them develop a life vision statement. In this episode Heather shares her story of working in HR and employee development and how seeing the incredible results of doing vision work in companies with their employees led her to begin doing it on the side for people in their personal li...
Welcome to What Works Wednesday! Last time, we talked about the crucial difference between tax preparers and tax planners. Tax planning isn't just for tax season—it's a year-round necessity, especially for self-employed professionals. Tax preparers focus on the past, while tax planners look ahead to minimize liabilities and align with long-term goals. Join us as we explore this vital topic further, empowering you to make informed financial decisions.
My guest on today’s podcast is TJ Van Gerven. TJ is the founder of Modern Wealth Builders, a financial planning and wealth management firm for high-earning millennial couples. In this episode TJ shares his story of entrepreneurship from starting off in a corporate setting to taking the leap of starting his own firm in the hopes of providing deeper value to the people he serves, at a lower cost, while still being able to provide a great living for himself. He discusses how he made some moves t...
Welcome to What Works Wednesday! Today, we're sharing last-minute tax tips for self-employed professionals. Learn how to leverage the tax code's incentives, plan strategically, and organize your finances effectively. Plus, discover the power of contributing to a self-employed retirement account before the filing deadline. Tune in for actionable strategies to optimize your taxes and secure your financial future, even in the final stretch of tax season.
My guest on today’s podcast is Zach Carlin. Zach is the owner of Summit Chasers Network, a business designed to help businesses lay the groundwork for enduring success, both personally and professionally. In this episode we talk about their SUMMIT system which stands for Start with you, Unify your team on a collective vision, Map your path, Make a clock, Increase talent density, and Time to scale. In this episode we talk in length about the importance of starting with working on your own grow...
My guest on today’s podcast is Evan Curtis. Evan is the Executive Director of Investments at Vanamor Investments, a real estate investment company that acquires middle market multifamily properties that are in need of rehabilitation with a long term investment horizon to obtain consistent cash flow and strong annual returns for their investors. In this episode Curtis shares his story from working at PIMCO in their fixed income and real estate investment business, to transitioning to working i...
Welcome to What Works Wednesday! Today, we're tackling estate planning and what happens to your money after you're gone. This episode breaks down the four primary ways money passes after death. From avoiding the risks of intestacy to ensuring your loved ones are cared for, Leland provides actionable insights to empower listeners. Join us as we confront the uncomfortable yet essential conversation about death and financial planning. Tune in now to start securing your family's future.
Welcome to this weeks “What Works Wednesday” episode as Leland tackles credit scores—essential for financial success. Join us as we decode their significance, unravel how they're calculated, and empower you to take control of your financial future. Tune in to What Works Wednesday and embark on a journey towards financial empowerment.
My guest on today’s podcast is Steve Coughran. Steve is the founder or Coltivar and Boosting Your Financial IQ. Coltivar is a business consulting and CFO service company that helps business owners get strategic and financial support to grow, turnaround, or sell their businesses. Boosting Your Financial IQ is a course and community that empowers people worldwide with the knowledge and skills to enhance their financial IQ, thereby fostering a global community of financially free individuals, by...
Welcome to this week's "What Works Wednesday" with Leland Gross. Today, amidst tax season, we're delving into the intricate world of taxes. Join us as we unravel the progressive tax system, exploring the importance of ongoing quarterly payments and the nuanced differences between marginal and effective tax rates. Discover why working with tax professionals is crucial for navigating this complex terrain and gain valuable insights to empower your financial journey. Tune in for a deeper understa...
Welcome to the 39th episode of the Self-Employment Success Podcast. My guest on today’s podcast is Bailey Feldman. Bailey is the founder of Fount and Flourish, a business whose mission is to redefine the female experience through a combination of their two pillars: Fount and Flourish. Through Fount they gather at events and their dedicated coworking space to build connections, share stories and skills, and enjoy and embrace the community of women. And through Flourish they grow through a comb...
Welcome to this week's "What Works Wednesday" episode as Leland delves into the intricacies of debt management. Join us as we explore efficient repayment strategies, including the debt avalanche and debt snowball methods. Then, discover how to make informed decisions about allocating extra funds between debt repayment and investments. Don't miss out on this insightful discussion that could reshape your financial future. Tune in and take the first step towards financial freedom.Links:PeaceLink...
Welcome to the 37th episode of the Self-Employment Success Podcast. My guest on today’s podcast is Jenna Epperly. Jenna is the founder of Jeneppfit, a personal training business for women in all stages of their life and body, that focuses not on before and after photos, or extreme all consuming strategies, but rather focuses on stewarding their bodies, honoring and cherishing them, so they can break free from body shame and diet culture, and embrace the truth that our bodies are good bodies i...
Welcome to this weeks “What Works Wednesday” episode as Leland discusses the Three-Bucket Account Structuring System. We dive into the short-term, middle-term, and long-term bucket system to understand how each can play a unique and pivotal role in optimizing your finances. Don't miss the chance to embrace this valuable tool, guiding you towards not just financial soundness but also a purpose-driven life where every dollar serves its intended purpose, grows efficiently, and contributes to you...
Welcome to the 35th episode of the Self-Employment Success Podcast. My guest on today’s podcast is Wes Barefoot. Wes is the founder of Path to Freedom, a business that helps people find freedom and take control of their lives through business ownership, specifically franchise ownership. Wes walks people through a tailored process to help them figure out what they truly want out of their life and career, and then matches them and walks with them through finding the right business that would al...
Welcome back to another episode of The Self-Employment Success Podcast. In today's What Works Wednesday installment, our host, Leland Gross, explores a crucial and often overlooked aspect of personal finances – your net worth. Join us as we unravel the significance of tracking your net worth, understanding its calculation, and how it serves as a vital metric for making informed financial decisions.PeaceLink Financial Planning LLC
Welcome back to the Self-Employment Success Podcast. My guest on today’s podcast is John Hewitt. John is the founder and owner of Loyalty Brands, a company that developed a business system that drives customer loyalty, repeat business, and financial stability for franchise owners. In John’s words the Loyalty Brand family of companies help build happy, successful, franchisees. You may recognize John’s name though from his previous business ventures including Jackson Hewitt Tax Services and Lib...
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