Tyler Olson, EA

Can AI replace a financial advisor?

It can run calculations & projections faster than any human

But financial planning has never been just about the math..

In today's episode, I talk about the value advisors bring and why the best outcomes often come from combining tools with thoughtful guidance

Community property rules are confusing

That does not mean you are doing anything wrong

It just means you need a plan and the right help

If you're married, have student loans, and live in a community property state, you need a student-loan-aware tax accountant

New episode out now:

If you’re in medicine, relocation is not a maybe, it’s a "when"

Med school. Residency. Fellowship. Attending.

Yet it still catches so many people off guard

Today's new episode is all about preparing for relocation and the costs that come with it

Listen on Apple or Spotify

New episode is out

I sat down again with Tyrone Ross to talk about the practicality of Bitcoin and blockchain

We talk about why sending money is still expensive, what “better rails” actually means, and why institutions are paying attention now

Listen on Apple or Spotify

This episode is about momentum

You graduate with big loans.
Your income jumps.
Life expenses stack up fast.

I share a 6-step roadmap for new attendings who want to build stability, invest early, and still enjoy their life along the way

Listen on Apple or Spotify

New episode is out

This one is for residents and fellows who are staring down the “what comes next” question

Academics, private practice, something in between..

No path is perfect and each has its tradeoffs

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If you’ve ever wondered whether you’re saving “enough,” this conversation will help you think about the question with more clarity and less pressure

Some households thrive saving 20%

Others do just fine saving less

From today’s new episode:

Best of luck to you both in your decisions!

You can usually opt to start paying in smaller segments if you wish. But it depends on your carrier and agent.

Who do you use?

You can make a less optimal financial decision and still be making a right one

You just have to understand the tradeoffs

Today's new episode is about two student loan scenarios where the math clearly pointed one way, but the better choice for the family pointed another

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One bad insurance decision can follow you for decades

In this week’s episode I share some thoughts about:

• Which disability insurance companies I trust
• Why some firms push the wrong products
• The GSI window most residents miss

Listen on Apple or Spotify

8 Pieces of Financial Advice for Your Fellowship Years Podcast Episode · A Good Problem to Have · 12/10/2025 · 19m

podcasts.apple.com/us/podcast/a...

If you’re starting fellowship this year, today’s new episode is for you

- Emergency funds
- Disability insurance
- Student loan strategy
- Home buying decisions

You want to create a system so managing your money doesn’t feel overwhelming

Listen on Apple or Spotify

Had a great conversation with Tyrone Ross about Bitcoin

No unnecessary hype or fear

Just a clear framework for understanding what it is and where it may fit

If you’ve felt curious but overwhelmed, today's new episode is the right place to start:

A text message that reads: “ You as well! Thank you for replying! It’s odd. He’s from Northwestern mutual, claimed he messaged me on Linkedin but I see no message from him (got another from some one in that group though many months back) Got a call last week insisting for a meeting, then got another phone call today confirming said meeting after I said to please only email me because I’m actively in patient encounters and it’s disruptive. I didn’t answer him for 3 business hours and that warranted a call I suppose? Definitely invasive I thought it was spam honestly”

So creepy, docs.

Being chased down by financial advisors?

Shut it down and seek advice from a real financial planner on your specific decisions when you need it.

Don’t let them try to fit their square peg into your round hole.

A lot of physicians ask:

“Do I actually need life insurance?”

The real question is:

“Who gets hurt financially if I’m gone?”

In today's new episode, Ronnie and I walk through when you need it, what kind, and how much:

Time with family

Less stress about taxes

Confidence your assets are protected

Just a few of the real returns on great financial planning

If you think financial planning is just about investments, you’re missing the big picture

It’s really about:

1) Saving time
2) Reducing taxes
3) Protecting what you’ve built

Today’s new episode breaks down these three pillars of real planning

Totally agree.

It's very gutted.

I still share things over there, but a lot of the people whose perspectives I looked forward to are either just gone or they're here.

I've tried to make a go of it here, but I just don't have the bandwidth.

The weekend twitter threads still get some good conversations going.

If you’re waiting to buy a home until rates drop, you could be waiting awhile

If you’re hoping for lower rates so you can refinance, you could put yourself in a tough spot

A great chat with Matt Graham about mortgages, the Fed, and how to make good decisions no matter the rates:

New episode of A Good Problem to Have is out

This one’s all about cash flow communication

Learning how to manage your spending in a way that keeps you intentional

Whether you're a couple or single, it's important to create the right systems

A few clients this summer asked the same question:

“Can we afford a pool?”

They weren’t short on net worth

They were short on liquidity

And it turned into one of the most interesting planning conversations we’ve had all year

From today's new episode:

A few clients this summer asked the same question:

“Can we afford a pool?”

They weren’t short on net worth

They were short on liquidity

And it turned into one of the most interesting planning conversations we’ve had all year

From today's new episode:

Physicians don’t need to retire early to win.

They just need the power to choose what “enough” looks like.

I've seen the difference in real life many times, and its HUGE.

That’s Financial Independence, Recreational Employment.

8. Protect Your Energy

Money buys options, not happiness.

The goal isn’t to hoard cash, it’s to own your time.

Don’t allow the pursuit of financial independence replace the reason you wanted it.

7. Redefine “Work”

Once you’re financially independent, work becomes recreational.

- Cut back to 0.8 FTE
- Do locums a few months a year
- Teach or consult
- Build something of your own

You’re not escaping medicine. You’re reshaping it.

6. Keep Investing Simple

No need for complexity.

Example allocation:

60% US Stocks
20% International
10% Real Estate
10% Bonds/Cash

Index funds. Low cost. Rebalance once a year.

I share this concept with my clients regularly - your returns come from time in the market not outsmarting the market

5. Plan for Health Insurance

The hidden cost of early freedom is healthcare.

Budget $25-35K/yr until Medicare.

Use ACA plans, private coverage, or part-time work benefits.

If you do consistent 1099 work, you can deduct the premiums.

It’s not a reason to quit the plan, just be prepared.

4. Build Tax Flexibility

Diversify where your money lives - pre-tax, Roth, and taxable.

That mix gives you total control in early retirement:

You can manage your bracket, convert to Roths, and fund your life w/o penalties.

Get to investing in these accounts as early in attendinghood as possible.