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.

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

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.

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

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.

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

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.

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

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.

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

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 common mistakes.

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

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)

• Why the “effective tax rate” savings method often falls short

• When annualizing your income makes sense (especially for seasonal earners)

• How to plan for Q1 payments now so you’re not scrambling later

• Why overpaying a little in Q4 might be better than under-saving all year

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 of clients navigating their retirement planning

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

In this episode, I cover key steps to make sure you’re financially prepared for the journey ahead. Some takeaways:

1. 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

2. 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

3. Creating an Estate Plan: Protect your family’s future and ensure your wishes are honored

4. Budgeting for Baby Expenses: How to adjust your budget to accommodate new expenses, including daycare and one-time costs for nursery essentials

5. Leveraging Dependent Care FSA: How to take advantage of pre-tax benefits for childcare expenses, which can save you money in the long run

6. Planning for Your Child’s Future: Various options for saving for your child’s education, including the benefits of 529 plans

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

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 & leveraging social media to attract clients
• The challenges of client relationships and the importance of knowing when to part ways
• Developing a successful client onboarding process

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✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.