Self-Employment Success Podcast

Welcome to What Works Wednesday! Today, we're covering the Fed's recent decision to lower interest rates by 50 basis points in September 2024. We'll quickly explain why rates change, how they impact borrowing and saving, and what this means for you. Let's dive in!

My guest on today’s podcast is Aakash Shah. He is the founder of Wyndly, an at home allergy testing and treatment company, designed to provide personalized immunotherapy treatment plans from real doctors delivered to your door. In this episode Aakash shares his journey which is truly remarkable. He shares about his struggle with allergies and realizing that much of the current healthcare system is...

In this episode of What Works Wednesday , Leland discusses how elections historically impact the stock market. Without diving into party politics, he explains the unpredictability of markets and shares insights on making informed investment decisions during election years, while emphasizing that no one can predict the future.

 My guest on today’s podcast is Briar Baughman. Briar is the owner and founder of Off-Load Moving, a moving company based out of Hampton Roads, Virginia. What’s unique about Briar is the level of success he has achieved in such a short time, being only 24 at the time of this recording. In this episode Briar shares his story. He details how his family moved 19 times in the first 18 years of his lif...

Welcome back to What Works Wednesday ! I’m Leland Gross, and today we're covering an often overlooked but crucial investing strategy: tax location . While asset allocation (diversifying investments) is well-known, tax location ensures you're maximizing after-tax returns by placing investments in the right accounts. It’s not just about what you make, but what you keep. So make sure your p...

My guest on today’s podcast is Melissa Broughton. Melissa is the founder of Busy Bee Advisors, a bookkeeping, accounting, and tax advisory firm for busy entrepreneurs and small businesses. What I love about Melissa is her own story of entrepreneurship. In this episode she shares about how she knew from a young age that she wanted to be an accountant and as an adult had a great career in accounting...

Welcome to this weeks What Works Wednesday ! Today, we're breaking down three common personal finance mistakes self-employed pros make—starting with the myth that you can deduct everything on your taxes. Tune in to avoid these costly mistakes!

My guest on today’s podcast is Garrett Delph. Garrett is the founder of Clarity Ops, a company that provides process and performance consulting and implementation for high impact organizations. What is unique about Garrett is his unique ability to help businesses navigate the complexities of expansion, due to his own experience running businesses and having his chairman of the board tell him that...

Welcome to What Works Wednesday! Today, we're highlighting a crucial concept: Information without implementation is useless. It’s not enough to have a solid financial plan or business strategy—what really matters is turning that knowledge into action. Without implementation, even the best advice or plan becomes wasted effort. Let’s focus on taking actionable steps to ensure that information d...

My guest on today’s podcast is Kate Moore. Kate is the founder of Melted and Moved, a boutique, luxury travel advisor business that provides travelers with tailor-made travel itineraries that deliver both luxury and a local touch world-wide. In this episode Kate shares her entrepreneurial journey. She shares how building a staffing agency from the ground up gave her 10 years of business experience...

Welcome back to What Works Wednesday! Today, I’m sharing why personal finance is more personal than just numbers. In my work with LLCs and other closely held businesses, I focus on how life’s transitions—like moving homes, starting a family, or managing aging parents—impact financial decisions. These personal moments shape our financial strategies and the freedom entrepreneurship offers. Let’s div...

My guest on today’s podcast is Daniel Shear. Daniel and his wife are the founders of Seasons Yield Farm, a Bakery & Farm in the Heart of the Shenandoah Valley of Virginia that offers organic, wood-fired, wild-leavened sourdough breads and pastries, whose mission is to connect their community with nourishing products, wonderful people, and the crafts of talented local artisans. In this episode...

Welcome to this week's What Works Wednesday! Today, we're diving into passive income. Despite the hype, there's a lot to unpack about what it truly means. We'll explore the definitions, pros and cons, and the differences between passive and active income. From real estate rentals to selling courses, we'll clarify misconceptions and highlight the real work involved. Join us...

My guest on today’s podcast is Nic Johnson. Nic is the founder of Listwise, a business designed to help home owners sell their home for the highest price possible, by creating incentive compensation for the real estate agent beyond the typical flat 3% model that has been in place for the last 100 years. They do this by aligning incentives, encouraging competition among agents, and therefore foster...

Welcome back to What Works Wednesday with your host, Leland Gross, and today we’re simplifying how investments make money. Investments typically generate returns in three ways: Dividends : Companies share profits with shareholders. Interest : Earned from lending money through bonds or savings accounts. Appreciation : Increase in the value of assets over time. Understanding these can help you make...

My guest on today’s podcast is JB Anderson. JB is the founder of Taxus Street Coffee, a local coffee shop and roastery located in Chesapeake Virginia. In this episode JB shares his story of entrepreneurship. Straight out of high school he started working as a personal trainer. After moving to Chesapeake Virginia to start a job with a ministry called Young Life, JB lived with some guys who taught h...

Welcome back to another episode of "What Works Wednesday" with your host, Leland Gross. This week, we're diving into a crucial topic for many parents: saving and planning for your kids' future. Whether it's college, trade school, or just ensuring they have a solid financial foundation, the options can be overwhelming. Leland breaks down three main methods to set up savings...

What does financial planning and photography have in common? More than I thought before this episode. Welcome to the Self-Employment Success Podcast. My guest on today’s podcast is William Leaton. William is the founder of William Sumner Photography, a wedding photography business located in Virginia. What’s unique about William is that he is only 3 months into running his business full time. In t...

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 m...

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 se...

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 com...

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 top...

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, wh...

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 secur...