In this episode, Ben Lake joins me to break down the biggest financial mistakes we see from wealthy families, business owners, and high income professionals every single year. We talk about the psychology behind investing, why so many people sit on massive amounts of cash, the dangers of concentrated stock positions, and why reacting emotionally to headlines almost always backfires.
In this episode, Ryan and I break down the actual systems we use with high-earning business owners to manage S-Corp cash flow the right way. We cover reasonable salary, monthly vs. quarterly distributions, tax planning mistakes we see all the time, and how to create a structure that actually works with your lifestyle and business. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com...
In this episode, Ben and I walk through the exact conversations we’re having with employees at companies preparing to go public. We talk about how to reduce taxes, create liquidity without selling everything, protect against downside risk, and avoid the mistakes we see people make after sudden wealth events. Whether you work at SpaceX, Anthropic, OpenAI, Databricks, Plaid, or another fast-growing private company, this is the framework I’d want you to hear before making any big decisions. -------...
In this episode, I walk through exactly what it looks like to work with a financial planner from start to finish. From organizing your entire financial life, to building a real plan, to ongoing decision making and accountability. If you've ever wondered what happens after you hire an advisor, this breaks it down step by step. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com ✅ ...
In this episode, I sat down with Dave McGhee, a business performance coach, to talk about why successful business owners hit plateaus, how coaching helps you see blind spots, and why growing your business often starts with getting clearer on what you actually want. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com ✅ My personal blog & newsletter: ...
In today’s episode, I walk through the exact ways I see clients use money to improve their lives, from outsourcing the things they hate to creating meaningful experiences and building real financial security. If you want your money to actually improve your life, this is the framework. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com ✅ My personal blog & newsletter: ...
In this episode, I sit down with Arda Bircan to break down how the short-term rental tax strategy actually works, who it’s for, and how high earners are using it to offset active income. But we also talk about the part most people ignore… how to make sure it’s actually a good investment. Because buying an Airbnb just for tax savings is a fast way to lose money. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com...
In this episode, Ryan and I go step by step through how to review your return, what numbers actually matter, and the biggest mistakes we see people make every year. From missing income documents to overpaying taxes & underpayment penalties, we cover what to look for so you don’t blindly sign something that could come back to bite you. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com ...
One of the biggest mistakes we see every year? People extend their taxes and think they can deal with it later. You can’t. Tax payments are still due in April. And if you don’t plan ahead, you could be looking at massive penalties, surprise balances, and a lot of unnecessary stress. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com ✅ My personal blog & newsletter: ...
In this episode, Blake and I break down what actually needs to happen after you sign your trust, how to fund it properly, and the common things we see people miss all the time. Because if your trust isn’t set up the right way, it might not work the way you think it will. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com ✅ My personal blog & newsletter: htt...
In this episode, I break down what financial health actually means, beyond just income or net worth. We’re talking about having a real financial plan, understanding your cash flow, maintaining a strong savings rate, building liquidity, and avoiding the mistakes I see even high earners make. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com ✅ My personal blog & newsletter: ...
In this episode, I walk through the exact framework we use with clients for their annual financial review. If you sit down once a year and go through these steps, you’ll have a much better understanding of where you are financially and where you’re going. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com ✅ My personal blog & newsletter: https://www.thomaskopelma...
In this episode, I’m joined again by Brent Sullivan to break down a strategy most investors have never heard of, but that can be incredibly powerful for the right situation: 351 exchanges If you’ve built significant wealth in a single stock, you’ve probably faced the same dilemma many high-net-worth investors deal with: Sell and diversify, but trigger a massive tax bill… or hold the position and take on concentration risk We walk through how 351 exchanges work, why they’ve started gaining moment...
In this episode, Ben Lake, CFA®, CFP® and I break down ILITs, Irrevocable Life Insurance Trusts, and why they matter for high net worth families. At a 40% federal rate above the exemption, that can mean writing a check for tens of millions of dollars. The real issue? Liquidity. If your net worth is tied up in a private business, real estate, or other illiquid assets, your family may not have the cash to pay the estate tax bill when it comes due. That can force a rushed sale, major discounts, or ...
I’ve built businesses. I work with business owners every day. And I’ve watched a lot of people romanticize buying one. So I wanted to have an honest conversation about it. David Barnett has helped people buy and sell dozens of companies, and he’s seen just about every mistake you can make. In this episode, we talk about why buying a business can be incredible… and how it can also completely wreck you if you overpay or structure it wrong. ------- ✅ Financial planning for 30-50 year old entreprene...
Private investments are one of the most talked-about areas of investing right now, but they’re also one of the most misunderstood. In this episode, Ben Lake and I break down how private investments actually work, including private equity, private real estate, and private credit, and more importantly, when they truly belong in a portfolio. Private investments can play an important role for the right investor at the right time, but they’re far from a requirement for building long-term wealth. ----...
In this episode, I chat with Brent Sullivan about how some of the wealthiest clients are using this strategy to offset huge capital gains, manage risk, and keep more of what they earn. We walk through real stories (like how one client saved $370,000 in taxes last year) and dig into why this strategy isn’t just about investments, it’s about smart financial planning. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com...
In this episode, I’m joined again by Ben Lake, CFA®, CFP® to talk through one of the most common real-world challenges we see with clients: needing liquidity, fast. Whether it’s a house that suddenly comes on the market, a business opportunity, or a life event that wasn’t neatly planned for, most people eventually face the question, “How do I actually get the cash?” We dig into borrowing strategies, HELOCs, margin loans, pledged asset lines, and when each one makes sense. ------- ✅ Financial pla...
In this episode, I brought back Ryan Dolan to talk through how to actually get ahead this year. We cover when you should hire a tax team, how to stay organized (without making it complicated), why extensions aren’t always a bad thing, and some of the most common mistakes we see around estimated payments. ------- ✅ Financial planning for 30-50 year old entrepreneurs: https://www.allstreetwealth.com ✅ My personal blog & newsletter: ...
In this episode, we walk through how to think about short term financial goals and where your cash should live while you are working toward them. We discuss common goals like buying a home, purchasing a car, funding college, or starting a business, and why chasing returns with short term money can derail those plans. If you have cash set aside for a goal in the next 1-3 years and aren't sure where it should sit, this episode will help you think through the right tradeoffs and avoid some very com...
It’s the start of a new year, and that means one thing for business owners and high-income earners: it’s time to dial in your Q4 tax strategy. In this episode, I’m joined by Ryan Dolan (licensed tax pro + advisor on our team) to break down everything you need to know about Q4 estimated payments , the 110% vs. 90% safe harbor rules , and how to avoid surprise tax bills or penalties in April. We cover: The difference between estimated payments and withholding (and how to use each strategically) Wh...
In this episode, we break down how to effectively manage your lifetime taxes & how they effect your investment decisions. Cody shares insights from his recent book, "Tax Planning to and Through Early Retirement," which has already sold over 8,000 copies. Some highlights: - Understanding your income sources in retirement - The impact of tax rates on your financial decisions - Strategies for maximizing tax efficiency through Roth conversions and traditional contributions - Real-life examples o...
In this episode, I cover key steps to make sure you’re financially prepared for the journey ahead. Some takeaways: Update Your Life Insurance : Why having proper life insurance is essential once you have a child and how to determine the right amount for your family Health Insurance for Your Newborn : The process of adding your baby to your health insurance plan and why it’s important to do this sooner than later Creating an Estate Plan : Protect your family’s future and ensure your wishes are ho...
In this episode, I sit down with my friend and fellow advisor, Mark Cecchini, to talk about what it takes to build a modern advisory career. We have similar practices today, but got here in completely different ways, so we walk through both paths and what we would do if we were starting over. Some highlights: Understanding your role as an advisor (whether as a lead advisor or a background planner) Finding your niche and how it can impact your business Strategies for building a personal brand &am...
In this episode, I sit down with Wes Gray to break down one of the most powerful and misunderstood tax strategies available moving to Puerto Rico under Act 60. Wes has lived there for years, so you’ll hear the real story behind the numbers, the rules, and the lifestyle. What we cover: What bona fide residency actually requires How 0% capital gains treatment is applied When the 4% business tax can make sense Lifestyle factors people forget to consider How to evaluate whether the move fits your si...
Most people neglect their taxes until it's too late, leaving money on the table. In this episode, I share strategies for managing your taxes before April, including: Understanding your projected income and quarterly payments Maximizing contributions to 401(k)s, HSAs, and 529 plans Utilizing tax loss harvesting and Roth conversions The impact of charitable giving and new AGI rules Reviewing your business entity structure for optimal tax benefits ---- ✅ Financial planning for 30-50 year old entrep...
Want to use real estate to cut your tax bill? In this episode I'm joined by CPA Nate Sosa to break down the real tax advantages of owning real estate, especially for business owners and high-income earners. You’ll learn: The difference between active and passive real estate tax treatment When real estate losses can (and can’t) offset your W-2 or business income How depreciation, bonus depreciation, and cost segregation work Why short-term rentals can be a powerful (but tricky) tax play The truth...
If you've ever wondered how to make the most out of your credit card rewards, this episode is for you. We break down how they can be a powerful tool for those looking to maximize their spending. Colin shares his thoughts on: Why Credit Cards Can Be Beneficial : Using credit cards responsibly and how they can offer significant advantages, especially for those with higher incomes The Basics of Earning Points : The benefits of cash back cards vs travel rewards cards Redemption Strategies : How to l...
In this episode, I break down the importance of understanding your pay stub. Many people overlook it, which can lead to missed tax opportunities, under-saving for retirement, and overpaying for benefits. Some highlights: Gross Pay: Understanding your full earnings before deductions Pre-Tax Deductions: How these can lower your taxable income and what to look for Taxes Withheld: Knowing your federal and state tax withholdings After-Tax Deductions: Mega Backdoor Roth 401k and ESPP Employer Benefits...
In this episode, I'm joined by Zach Ashburn to discuss the intersection of financial planning and personal freedom. Some highlights: The journey from corporate life to entrepreneurship How effective financial planning can empower you to make life-changing decisions The importance of liquidity and cash flow in achieving your ideal lifestyle Real-life stories of how financial planning has transformed lives (including Zach's experience as a foster parent and the impact it had on his family's decisi...
