The Long Game

Thomas Kopelman
undefined
Sep 5, 2025 • 31min

Donating Private Assets to a Donor Advised Fund (with Brad Caswell)

In this episode, I'm joined joined by Brad Caswell, an expert in the world of Donor Advised Funds (DAFs). He served as the Chief Operating Officer of Vanguard Charitable for 12 years, and now as a consultant helping organizations and individuals navigate the complexities of charitable giving. Some highlights from the episode:The benefits of using DAFs (including tax advantages and the ability to donate complex assets like real estate)The process of donating private assets and how to maximize your charitable contributionsHow to strategically time your donations to align with life events (such as selling a business or receiving an inheritance)To find Brad: Charitable Solutions LLC-------------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.
undefined
Aug 29, 2025 • 22min

Stock vs Asset Sale: Considerations for Business Sale (with Chad Huebsch, EA, CTP)

In this episode, I'm joined by tax expert Chad Huebsch for a deep dive into the difference between stock and asset sales. If you're a business owner considering selling your business, understanding these two types of sales is essential, as they have significant tax implications. You'll learn about:How different industries approach these salesThe significance of goodwill in business transactionsPlanning strategies to maximize your after-tax proceedsThe hybrid 338(h)(10) election and its benefitsThe importance of having solid financials before selling-------------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.
undefined
Aug 22, 2025 • 24min

Financial Planning from 30-50 Years Old: Key Decisions to Get Right

In this episode, we dive deep into financial planning for individuals in their 30s-50s. We break down the unique challenges & opportunities that start to come up during this stage of life, including:Navigating cash flow and lifestyle creepMaking informed housing decisions in today's marketBalancing family responsibilities while planning for the futureThe importance of education funding and estate planningStrategies for effective investment and risk management-------------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.
undefined
Aug 15, 2025 • 34min

IULs: How They're Incorrectly Sold & Used (with Robert Rikard)

In this episode, I'm joined by Robert Rikard, a lawyer and partner at the Investor Loss Center, to discuss the controversial world of Index Universal Life (IUL) insurance. With the rise of social media influencers promoting IULs, many people are confused and misinformed about these products.He explains how many agents misrepresent these products, often targeting middle America with unrealistic promises of tax-free retirement income. Some highlights from the episode:The rise of IULs and the misinformation surrounding themThe commission structure that incentivizes agents to sell IULsReal-life case studies of clients who have suffered significant lossesAlternatives to IULs that may be more suitable for average investorsWebsite: https://www.investorlosscenter.comLinkedIn-------------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.
undefined
Aug 8, 2025 • 27min

SBA Loans Explained (with Matthias Smith)

In this episode, I sit down with Matthias Smith (founder and owner of Pioneer Capital Advisory) a brokerage firm specializing in SBA loans. We talk about:- The different types of loans available for purchasing a business- What an SBA loan is and how it works- The importance of personal guarantees and life insurance in the loan process- Common misconceptions about SBA loans- Tips for prospective business buyers on preparing for the loan processConnect with Matthias:Email – matthias@pioneercap.comLinkedIn – Matthias SmithTwitter – @SBA_Matthias-------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.
undefined
Aug 1, 2025 • 31min

Planning for an IPO (with Mark Cecchini, CFP®)

In this episode, I'm joined by Mark Cecchini, CFP® to discuss the intricacies of planning for an IPO. As the window opens up again, many employees are facing similar situations. We dive deep into the essential steps for preparing for an IPO, including:Understanding the difference between single-trigger and double-trigger RSUsThe importance of having a solid financial plan and clear goalsStrategies for managing equity concentration and diversificationTax planning considerations before and after an IPOThe significance of Qualified Small Business Stock (QSBS) eligibility--------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.
undefined
Jul 25, 2025 • 15min

Answering Listener-Submitted Questions

Curious about retirement accounts? Dive into the differences between Roth and traditional IRAs and learn why solo 401(k)s might win over SEP IRAs for entrepreneurs. Discover savvy tax reduction strategies for W-2 employees and weigh the decision of paying off that mortgage versus investing. The conversation emphasizes a long-term view on finances, helping you balance emotional choices with logical financial strategies.
undefined
Jul 18, 2025 • 43min

Tax Strategies for $1M to $10M SMB Owners (with Chad Huebsch, EA, CTP)

In this episode, I'm joined by Chad Huebsch from Blueprint Tax to break down the importance of tax planning for business owners doing $1 million to $10 million. Chad shares valuable insights on entity selection, including the pros and cons of sole proprietorships, S-corporations, partnerships, and C-corporations. Some highlights:PTET (Pass-Through Entity Tax): How to maximize deductions for state and local taxesQBI (Qualified Business Income) Deduction: Understanding the thresholds and how to optimize your tax situationRetirement Planning: Exploring options like 401(k)s and cash balance plans to save on taxes while preparing for the futureHiring Family Members: The benefits and considerations of paying your children or spouse for work in your businessReal Estate Strategies: Using short-term rentals and property ownership to offset income-------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.
undefined
Jul 11, 2025 • 50min

Big Beautiful Bill Summarized: Tax Cuts, Tips, SALT Caps, PTET, and More

In this episode, I’m joined by tax expert Roger Ledbetter to break down the recent tax bill. We talk about the new rules and discuss its potential impact on both individuals and businesses. Some highlights:Key topics include:Changes to individual tax rates and deductions, including the standard deduction and child tax creditThe implications of the bill for business owners, including QBI and bonus depreciationNew deductions for tips, overtime, and car loan interestInsights on Opportunity Zones and Qualified Small Business Stock (QSBS)----------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.
undefined
Jun 27, 2025 • 9min

Hiring Children & Spouses: Is This A Good Or Bad Idea?

In this episode, I break down the ins and outs of hiring your children, spouse, and even other family members. Some highlights:Hiring Your Kids: The age at which your children can contribute meaningfully to your business and how you can set them up for financial success through tools like Roth IRAs and 529 plansThe Benefits of Hiring Your Spouse: How to maximize contributions to retirement accounts and the tax benefits that come with itNavigating Family Dynamics: I share my personal experiences and insights on what makes a successful working relationship and the potential mistakes to avoidTax Planning Tools: How to ensure that your hiring practices are compliant and beneficial for your tax situation, helping you set up your family for future success.--------------------------------------✅ Financial planning for 30-50 year old entrepreneurs: ⁠⁠⁠⁠⁠⁠⁠https://www.allstreetwealth.com⁠⁠⁠⁠⁠⁠⁠⁠⁠✅ My personal blog & newsletter: ⁠⁠⁠⁠⁠⁠⁠https://www.thomaskopelman.com⁠⁠⁠⁠⁠⁠⁠⁠⁠Disclaimer: None of this should be seen as financial advice. It is just for informational purposes.

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app