Podcast
The Long Game
Hosted by Thomas Kopelman · EN
The Long Game podcast is all about educating 30-50 year old business owners and those with equity compensation on how to build wealth.
You will learn everything from the basics to complex tax, estate, and financial planning concepts from Thomas Kopelman as well as other qualified professionals.
25episodes
Episodes
Newest firstAll episodes
"Should I Turn My Primary Residence into a Rental?"
5d ago00:15:16Tap to summarizeFor a lot of people, the answer isn't as straightforward as comparing rent to the mortgage payment.In this episode, I break down the key factors I look at when helping clients make this decision, including equity, cash flow, capital gains taxes, future home purchases, and whether owning rentals actually fits into your long-term financial plan.---------✅ 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.
Transcribe →How to Withdraw from Your Portfolio in Retirement (+ Common Misconceptions)
2w ago00:27:11Tap to summarizeIn this episode, Ben and I break down the retirement income strategies we use with clients, including:How to coordinate taxable, pre-tax, and Roth accountsWhen Roth conversions make senseSocial security timingAnd moreIf you've worked hard to build wealth, this episode will help you think about how to make it last.---------✅ 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.
Transcribe →Biggest Financial Regrets of the Wealthy (w/ Ben Lake)
3w ago00:28:00Tap to summarizeIn 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.-------✅ 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.
Transcribe →How to Manage Salary & Distributions in Your S Corp
4w ago00:17:41Tap to summarizeIn 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✅ My personal blog & newsletter: https://www.thomaskopelman.comDisclaimer: None of this should be seen as financial advice. It is just for informational purposes.
Transcribe →Planning for an IPO: 8 Things to Think About
May 1500:38:12Tap to summarizeIn 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.-------✅ 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.
Transcribe →What It’s Actually Like Working with a Financial Advisor (Step-by-Step)
May 800:12:28Tap to summarizeIn 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✅ My personal blog & newsletter: https://www.thomaskopelman.comDisclaimer: None of this should be seen as financial advice. It is just for informational purposes.
Transcribe →The Value of Hiring Coaches (with Dave McGhee)
May 100:30:34Tap to summarizeIn 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: https://www.thomaskopelman.comDisclaimer: None of this should be seen as financial advice. It is just for informational purposes.
Transcribe →Does More Money Make You Happier?
Apr 2400:10:24Tap to summarizeIn 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: https://www.thomaskopelman.comDisclaimer: None of this should be seen as financial advice. It is just for informational purposes.
Transcribe →Short Term Rentals: Tax Benefits & How To Find Good Investments (with Arda Bircan)
Apr 1700:24:35Tap to summarizeIn 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✅ My personal blog & newsletter: https://www.thomaskopelman.comDisclaimer: None of this should be seen as financial advice. It is just for informational purposes.
Transcribe →How to Review Your Tax Return (with Ryan Dolan)
Apr 1000:17:15Tap to summarizeIn 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✅ My personal blog & newsletter: https://www.thomaskopelman.comDisclaimer: None of this should be seen as financial advice. It is just for informational purposes.
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