Self-Employment Success Podcast
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!
Episodes
70 episodes
Episode 70: What Works Wednesday: The Effects Of The Fed Lowering Interest Rates
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...
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12:57
Episode 69: Rising Tides, Forcing Mechanisms, and Keys To Entrepreneurship W/ Aakash Shah
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 episo...
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39:48
Episode 68: What Works Wednesday: How Elections Impact The Stock Market
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 invest...
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13:50
Episode 67- Goals that are big enough for everyone else’s goals w/ Briar Baughman
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 ...
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55:57
Episode 66: What Works Wednesday- It’s Not About What You Make, But What You Keep
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 ens...
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13:32
Episode 65: Helping Entrepreneurs Face The Monster Under The Bed W/Melissa Broughton
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 entrep...
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48:22
Episode 64: What Works Wednesday- 3 Financial Planning Misconceptions I See Self-Employed Professionals Make
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 mi...
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13:13
Episode 63: Flourishing Your Business Through People, Processes, and Performance w/ Garrett Delph
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 abil...
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48:29
Episode 62: What Works Wednesday: Information without implementation is useless
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 knowle...
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16:06
Episode 61: Fostering Luxurious Experiences With A Local Touch w/ Kate Moore
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....
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42:16
Episode 60: Personal Finance Is More Personal Than It Is Finance
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...
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13:34
Episode 59: Building Community Around Bread Day W/Daniel Shear
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 an...
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54:41
Episode 58: Passive Income Is Not As Passive As You Think
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 act...
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12:54
Episode 57: Aligning Incentives With Your Real Estate Agent W/ Nic Johnson
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 typic...
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47:39
Episode 56: What Works Wednesday: The Three Ways Investments Make Money
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 shar...
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11:56
Episode 55: Roasting Coffee As A Way To Care For Yourself And Others W/ JB Anderson
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 st...
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54:51
Episode 54: What Works Wednesday: Building Generational Wealth, Three Ways To Save For Your Child’s Future
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 ensuri...
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15:15
Episode 53: Vision, Legacy, and Photography W/ William Leaton
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 Pho...
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53:21
Episode 52: What Works Wednesday: Three Tax Breaks In One, The Health Savings Account Explained
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 tripl...
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13:38
Episode 51- Finding Success In Helping Others Foster Success W/ Hannah Johnson
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. I...
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55:54
Episode 50: What Works Wednesday: The 2.5 Things You Can Do With An Old 401k
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 a...
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15:54
Episode 49: Vision, Agency, And Purpose: Developing A Vision Statement For Your Life W/ Heather Fischer
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 ...
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45:04
Episode 48: What Works Wednesday: Tax Preparation Vs. Tax Planning
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 prepa...
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10:37
Episode 47: The Pursuit of Continuous Improvement with TJ Van Gerven
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 star...
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43:31
Episode 46: What Works Wednesday: Things You Can STILL Do To Lower Last Year’s Taxes
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...
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11:59