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Grant Bledsoe Financial Planner to Business Owners

I'm a financial planner to business owners, and the founder of Three Oaks Wealth. Our firm helps business owners align their business interests with their personal finances, often including the exit or sale of equity holdings.

I hold several professional credentials, including the CERTIFIED FINANCIAL PLANNER™, Chartered Financial Analyst, and Certified Exit Planning Advisor designations.

Recent Content

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Ep #250 - Should I Roll My 401K Into An Ira? &Raquo; Grow Money Business 2022
Ep #250 – Should I Roll My 401k Into an IRA?

Most Americans have at least some of their Retirement savings sitting in workplace retirement plans like 401ks, 403bs, SEP-IRAs and the like.  And when you leave a job, due to a retirement transition…

Most Americans have …

Most Americans have at least some of their retirement savings sitting in workplace retirement plans like 401ks, 403bs, SEP-IRAs and the like.  And when you leave a job, due to a retirement transition or not, many people wonder what they should do with the savings they’ve accumulated in the plans.  We’ve noticed that the more people tend to have in their retirement plans, the more reluctant they are to take action out of fear of making a mistake.  In this episode of the podcast we’ll answer several questions about 401k rollovers: ·       Should I keep my savings in the 401k or…

Listen · 50:38
Ep #249 - We Just Retired. Should We Downsize? &Raquo; Grow Money Business 2022
Ep #249 – We Just Retired. Should We Downsize?

Downsizing from your large, long-held family home is a popular concept for retirees, but may not always be the best choice.  Even though smaller homes are less costly & easier to maintain, giving…

Downsizing from your…

Downsizing from your large, long-held family home is a popular concept for retirees, but may not always be the best choice.  Even though smaller homes are less costly & easier to maintain, giving up your family's major meeting venue may not be the best choice.  This week we respond to a listener question on whether downsizing might be right for them, and cover Nvidia's recent earnings call and an article about the prevalence of gift card scams.   Highlights [05.30] Market Update – News on Nvidia earnings. [11.24] Article of the Week – This week’s article on gift card fraud. …

Listen · 26:17
Ep #248 - I’d Like To Give More To Charity. How Can I Reduce My Taxes By Doing So? &Raquo; Grow Money Business 2022
Ep #248 – I’d Like to Give More to Charity. How Can I Reduce My Taxes by Doing So?

Mailbag Question: “I’d like to give more Money to a couple different charities this year, but my tax person said it wouldn’t help my taxes.  Is there a way I can make a gift that reduces my tax…

Mailbag Question: …

Mailbag Question: “I’d like to give more money to a couple different charities this year, but my tax person said it wouldn’t help my taxes.  Is there a way I can make a gift that reduces my taxes?”   Intro: “There are a ton of different ways to give to charity, but not all of them will help you on your taxes.  This week we cover a listener question about tax efficient charitable giving, and when it will or will not help you.”   Resources: Donor-Advised Funds (DAFs): What They Are and How They Work nerdwallet.com/article/taxes/donor-advised-funds   Qualified Charitable Distribu…

Listen · 27:39
Ep #247 - Should I File For Social Security Before It Runs Out? &Raquo; Grow Money Business 2022
Ep #247 – Should I File for Social Security Before It Runs Out?

Mailbag Question: “Everything I hear about Social Security is bad, and it sounds like the program will run out of money in a few years.  Is there a good reason I shouldn’t file for benefits now b…

Mailbag Question: …

Mailbag Question: “Everything I hear about Social Security is bad, and it sounds like the program will run out of money in a few years.  Is there a good reason I shouldn’t file for benefits now before the money runs out?”   Intro: “Many retirees are concerned about the state of Social Security, and some of them even expect the program to crumble in the next few years.  Does that mean you should get your money out now before it does?  This week we respond to a listener question about by explaining what’s going on with Social Security, how long it’ll be before the Social Security…

Listen · 33:02
Ep #246 - Using Tech Tools To Bypass Irs Hold Times With Tomas Nally &Raquo; Grow Money Business 2022
Ep #246 – Using Tech Tools to Bypass IRS Hold Times with Tomas Nally

It’s no secret that the IRS is underfunded right now.  It takes most taxpayers months to receive refund checks, and most would rather go to the dentist than wait on hold to talk with the IRS.  Our…

It’s no secret tha…

It’s no secret that the IRS is underfunded right now.  It takes most taxpayers months to receive refund checks, and most would rather go to the dentist than wait on hold to talk with the IRS.  Our guest this week is Tom Nally, who’s recently launched Tax Now to help taxpayers and their professionals navigate this landscape.  The platform syncs up with the IRS database and simply notifies you when there are updates to your account.  It’s a sorely needed tool, and Tom walks us through what he’s built and how the launch has gone. We also cover an article about Trump’s interest in al…

Listen · 58:21
Ep #245 - Should We Move To Tennessee, Texas, Or Florida To Reduce Costs In Retirement? &Raquo; Grow Money Business 2022
Ep #245 – Should We Move to Tennessee, Texas, or Florida to Reduce Costs in Retirement?

Mailbag question: “My husband and I are assembling our retirement plan and planning to relocate once I quit working.  We’re trying to decide between Tennessee, Florida and Texas, since they’re …

Mailbag question: …

Mailbag question: “My husband and I are assembling our retirement plan and planning to relocate once I quit working.  We’re trying to decide between Tennessee, Florida and Texas, since they’re all states with lower tax and retirement Lifestyle costs.  Which do you think is best?  The lists are all different.”   Intro: Financial media love to create lists of the “best” and “lowest cost” states to retire in.  This week we answer a question about the differences between Tennessee, Texas, and Florida as retirement destinations, and what you should consider when relocating in r…

Listen · 21:17
Ep #244 - Do I Really Need A Living Trust? &Raquo; Grow Money Business 2022
Ep #244 – Do I Really Need a Living Trust?

  Mailbag Question: “I recently met with an attorney to get my estate plan done.  They recommended that I create a living trust to hold some investments and my house.  Is that legitimate?  It so…

  Mailbag Question:…

  Mailbag Question: “I recently met with an attorney to get my estate plan done.  They recommended that I create a living trust to hold some investments and my house.  Is that legitimate?  It sounds like an upsell better suited for very rich people.”   Intro: This week on Grow Money Business we answer a listener questions about trusts and estate planning.  Our faithful listener spoke with an attorney about estate planning recently, who recommended a living trust as part of his plan.  We cover the pros and cons of living trusts and whether the recommendation is an upsell from the att…

Listen · 32:09
Ep #243 - I’d Like To Retire Early But I’m Concerned About The Penalties &Raquo; Grow Money Business 2022
Ep #243 – I’d Like to Retire Early but I’m Concerned About the Penalties

Early retirement is a popular goal for many, but actually making it happen can be challenging.  One major obstacle is the early withdrawal penalty imposed to distributions from IRAs & 401ks befor…

Early retirement is …

Early retirement is a popular goal for many, but actually making it happen can be challenging.  One major obstacle is the early withdrawal penalty imposed to distributions from IRAs & 401ks before 59 ½ years of age. This week on the show we answer a listener question about how to navigate this landscape and a few possible workarounds.  We also cover whether index Investing has impacted the markets, and an article about how inflows to hot investment funds can falsely influence performance numbers   Resources: GMO: Passive Investing’s Impact Has Been Overblown, But It’s Not Negligibl…

Listen · 34:38
Ep #242 - Why Would I Ever Want To Invest In Other Countries? &Raquo; Grow Money Business 2022
Ep #242 – Why Would I Ever Want to Invest in Other Countries?

One question we get a lot is why we’d ever want to invest in countries other than the U.S.  The U.S. stock market has done far better than other countries recently.  It’s the biggest national ma…

One question we get …

One question we get a lot is why we’d ever want to invest in countries other than the U.S.  The U.S. stock market has done far better than other countries recently.  It’s the biggest national market in the world.  The U.S. has the strongest, most resilient Economy.  And the U.S. dollar is the world’s reserve currency.  Why would we ever want to invest anywhere else?  This week on the show we cover this question in detail, June’s inflation data, and an article on the impact that inflation has on bond markets.   Links: https://www.dimensional.com/us-en/insights/global-diversifica…

Listen · 26:30
Ep #241 - Should I Invest In Bitcoin Etfs? &Raquo; Grow Money Business 2022
Ep #241 – Should I Invest in Bitcoin ETFs?

Mailbag Questions: 1)         “I’m a small business owner, and have a SEP-IRA that I’d contributed to annually until a few years ago.  Then things got tight during COVID and I took a …

Mailbag Questions: …

Mailbag Questions: 1)         “I’m a small business owner, and have a SEP-IRA that I’d contributed to annually until a few years ago.  Then things got tight during COVID and I took a break from making contributions.  Now business is turning around again.  I’ve been watching the bitcoin ETFs and am wondering if this is a good investment once I start putting money into my plan again.”  

Listen · 31:28
Ep #240 - What Should I Do With The $850,000 Inheritance I Just Received?” &Raquo; Grow Money Business 2022
Ep #240 – What Should I Do With the $850,000 Inheritance I Just Received?”

This week we cover a listener question about how to handle an inheritance of $850,000.  Jason recently dropped the question in our mailbag after receiving the inheritance unexpectedly.  He and his w…

This week we cover a…

This week we cover a listener question about how to handle an inheritance of $850,000.  Jason recently dropped the question in our mailbag after receiving the inheritance unexpectedly.  He and his wife are in a stable financial situation and aren’t sure what to do next.  Grant shares his thoughts on what the couple should do. We also review an article in The Atlantic covering whether monetary policy actually works in practice, and the presidential debate after a relatively quiet week in the markets.   Resources: https://www.theatlantic.com/ideas/archive/2024/06/interest-rates-inflation/6…

Listen · 15:27
Ep #239 - The Secret Sauce Of Buying &Amp; Selling Businesses With Jeremy Harbour And Us Stock Market Concentration &Raquo; Grow Money Business 2022
Ep #239 – The Secret Sauce of Buying & Selling Businesses with Jeremy Harbour and US Stock Market Concentration

Our guest on the show this week is Jeremy Harbour.  Jeremy has been involved in the M&A market across the globe for decades.  He’s the founder and CEO of the Unity Group, a boutique internatio…

Our guest on the sho…

Our guest on the show this week is Jeremy Harbour.  Jeremy has been involved in the M&A market across the globe for decades.  He’s the founder and CEO of the Unity Group, a boutique international mergers & acquisitions firm.  He also runs the Harbour Club, a professional network focused on teaching M&A best practices to entrepreneurs.  Jeremy shares with us the do’s and don’ts and buying and selling businesses after dozens of successes and failures he’s had over the years.  We also cover an article by Global Financial Data that reviews concentration in the US stock mar…

Listen · 46:00
Ep #238 - Should I Adjust My Withholdings This Year? &Raquo; Grow Money Business 2022
Ep #238 – Should I Adjust My Withholdings This Year?

We dedicated this week’s episode to another mailbag question from our listeners related to tax withholdings.  Here in the U.S., most people set some money aside throughout the year from their incom…

We dedicated this we…

We dedicated this week’s episode to another mailbag question from our listeners related to tax withholdings.  Here in the U.S., most people set some money aside throughout the year from their income and/or estimated tax payments, to be put toward their income tax bill for the year.  Then they cross their fingers when it comes time to file their return, hoping that they don’t owe any more than what they’ve set aside. In this week’s episode Grant covers the ins and outs of tax withholdings, and answers a listener’s question on whether they should adjust their withholdings for 2024.…

Listen · 16:55
Ep #237 - Michelle Seiler Tucker On Business Valuations &Amp; Interest Rates &Raquo; Grow Money Business 2022
Ep #237 – Michelle Seiler Tucker on Business Valuations & Interest Rates

Michelle Seiler Tucker is back on the show this week to discuss how higher interest rates have impacted the market climate for business sales.  Michelle is the best selling author of Exit Rich and ha…

Michelle Seiler Tuck…

Michelle Seiler Tucker is back on the show this week to discuss how higher interest rates have impacted the market climate for business sales.  Michelle is the best selling author of Exit Rich and has been in the M&A business for over 20 years (selling over 1,000 business over that time frame).  She shares a few basics of what business owners can do now to set themselves up for future success, as well as how the buyer’s perspective has changed. We also cover some market news.  Gamestop has been in the news recently after Keith Gill, aka “Roaring Kitty” posted screenshots of his ho…

Listen · 59:11
Ep #236 - The Trump Verdict, T+1 Trade Settlement, And Special Purpose Acquisition Companies &Raquo; Grow Money Business 2022
Ep #236 – The Trump Verdict, T+1 Trade Settlement, and Special Purpose Acquisition Companies

This week was relatively slow in market news…..until the Trump verdict came out.  Donald Trump was found guilty on all 34 counts brought against him in the hush money trial, which throws more uncer…

This week was relati…

This week was relatively slow in market news…..until the Trump verdict came out.  Donald Trump was found guilty on all 34 counts brought against him in the hush money trial, which throws more uncertainty into upcoming election cycle.  The financial world changed on Tuesday as well, as the stock settlement cycle was shortened from T+2 to T+1.  We cover what all this means for you, how the markets reacted to the Trump verdict, and whether the investment vehicle Trump used to take Truth Social public is something you should consider for your portfolio. Resources: https://www.jpmorgan.com/ins…

Listen · 32:14
Ep #235 - The Three Golden Rules Of Investing &Raquo; Grow Money Business 2022
Ep #235 – The Three Golden Rules of Investing

We’ve covered a lot of technical investment concepts on the show over the last couple years.  Since it’s sometimes helpful to take a step back and focus on the core foundational concepts, this we…

We’ve covered a lo…

We’ve covered a lot of technical investment concepts on the show over the last couple years.  Since it’s sometimes helpful to take a step back and focus on the core foundational concepts, this week’s episode covers the three golden rules of investing we should all be trying to use.  We also cover Nvidia’s stock split and the new world of financial scammers. Resources sherwood.news/tech/investigating-instagram-investing-scams/

Listen · 49:35
Ep #234 - Is It Possible To Live Off Dividend Income Alone In Retirement? &Raquo; Grow Money Business 2022
Ep #234 – Is It Possible to Live Off Dividend Income Alone in Retirement?

A few weeks ago I had someone ask whether it was possible to live off of dividend income alone in retirement.  This gentleman had saved up a nice chunk of money and was currently invested 100% in sto…

A few weeks ago I ha…

A few weeks ago I had someone ask whether it was possible to live off of dividend income alone in retirement.  This gentleman had saved up a nice chunk of money and was currently invested 100% in stocks.  He was eligible for Social Security benefits, and was intent on never selling any of his shares in retirement. Instead, he wanted to live off the dividends his portfolio produced to pay his expenses.  He thought that between his Social Security benefits and dividend income he’d have plenty to pay his bills.  I thought this was an interesting question, and dive into the details in today…

Listen · 39:47
Ep #233 - Why Am I Getting These Annoying Amended 1099S Every Year? What Can I Do About It? &Raquo; Grow Money Business 2022
Ep #233 – Why Am I Getting These Annoying Amended 1099s Every Year? What Can I Do About It?

We’re trying a new format on the show!  Starting this week each episode of Grow Money Business will include a few consistent sections.  We’ll answer mailbag questions.  We’ll interview guests…

We’re trying a new…

We’re trying a new format on the show!  Starting this week each episode of Grow Money Business will include a few consistent sections.  We’ll answer mailbag questions.  We’ll interview guests.  We’ll spend a couple minutes reviewing the markets.  And we’ll review news articles you should be paying attention to.  Enjoy! Resources: etf.com/sections/news/fidelity-adds-surcharge-etf-platform wsj.com/personal-Finance/retirement/inherited-retirement-account-ira-irs-c3c95273?mod=personal-finance_lead_story  

Listen · 41:18

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