White Coat Investor Podcast – Milestones to Millionaire #254: Hospitalist Becomes a Full-Time Entrepreneur & Finance 101: Tax Loss Harvesting
Released: December 22, 2025
Host: Dr. Jim Dahle
Guest: “Jay,” Physician-Hospitalist Turned Entrepreneur

Episode Overview

This episode spotlights Jay, a hospitalist from San Diego who transformed his career—transitioning from clinical medicine to building a substantial entrepreneurial empire, primarily through acquiring and managing car wash businesses. Jay shares his path to a net worth exceeding $8 million less than a decade after residency, emphasizing the power of entrepreneurship, deliberate risk-taking, smart investing, and balancing life priorities. After the interview, Dr. Dahle delivers a concise yet practical primer on tax loss harvesting, designed for high-income medical professionals looking to optimize their investment returns.

Key Discussion Points & Insights

1. Introduction to Jay and His Decision to Leave Clinical Partnership

• Jay shares his background: 39 years old, completed training in 2017, practicing in San Diego.
• He announces his recent milestone: Leaving his hospitalist group before a ten-year vesting mark to focus on new business ventures.

Quote [02:20]:

“I have decided to give up my partnership at my practice before the 10 year mark, before I get vested and I’m switching to different business ventures.” — Jay

2. Financial Snapshot: Net Worth and Asset Breakdown

• Jay provides a detailed breakdown of his net worth, now approximately $8.5 million, comprising:
  • Business and Real Estate: $4 million (primarily car washes)
  • Retirement Accounts: $2.8 million (self and spouse)
  • Bitcoin: $1.5 million
  • Emergency Fund/Savings: $100,000+
  • Physical Gold & Jewelry
• He’s acquired six car washes with a partner, with three more acquisitions underway.

Quote [03:15]:

“It’s probably eight and a half million dollars...about 4 million of that is in business and real estate...I have 1.5 million in a Bitcoin position...2.8 million in retirement...and I've got some physical gold and jewelry.” — Jay

3. Entrepreneurial Drive and Early Influences

• Jay attributes his entrepreneurial spirit to childhood experiences (family instability, exposure to business through his father, starting a tutoring company in high school).
• Money was a sensitive topic at home; the motivation to master finances stemmed from both hardship and ambition.

Quote [04:10]:

“My dad was in business. I always kind of had like a little bit of a business knack...I think money became really important and I started to understand it more. It wasn’t really talked about in my family…it kind of made me want to understand money and in business and go into that.” — Jay

4. Transition from Medicine to Car Wash Empire

• Jay explains he’s not leaving medicine entirely but now picks up hospitalist shifts on his terms—choosing flexibility and time for his young family.
• His entrepreneurial awakening coincided with seeking ways to build a legacy, gaining financial and time freedom.

Quote [05:16]:

“I’m going to practice kind of on my own terms now...I get to build a legacy there that I get to actually pass down to my kids and my family going forward.” — Jay

5. Student Loans, Leverage, and Early Risk-Taking

• Jay graduated with $370,000 in medical school debt.
• Before his first paycheck as an attending, he used a physician loan to buy a house, racking up $1.1 million in total debt.
• From the start, Jay was comfortable with leverage and risk, using it to accelerate wealth-building.

Quote [06:54]:

“I leveraged my contract to go buy a home on a doctor's loan...literally before my first paycheck, like $1.1 million total in debt before I had even my first paycheck.” — Jay

6. Real Estate to Business Ownership

• Early wealth-building involved heavy medical work and aggressive savings.
• Ground-up real estate developments proved lucrative but were capital- and time-intensive, especially as market dynamics changed.
• Proceeds were recycled into personal aims (buying a beach home) and high-conviction investments (Bitcoin).
• Facing large tax bills, Jay explored business ownership for bonus depreciation—leading to large-scale car wash acquisitions, returning substantial tax benefits.

Quote [08:58]:

“My biggest liability was my taxes...it led me down the route of business...I discovered bonus depreciation through car washes that eventually were able to literally wipe out a six figure tax bill every year. And so I've been doing that and compounding that with a partner.” — Jay

7. Leverage, Debt, and Risk Management

• Jay’s debts: Car washes ($7M debt, worth $14M), personal home ($1.4M), student loans, HELOC used for car wash purchases.
• Jay is comfortable with strategically managed debt: “If I know I can weather a bear market or say 50% down year back to back and they still cash flow and they make sense, I’m still going to buy those with debt because it’s just an intelligent way to leverage.”

Quote [11:01]:

“I don’t think I’m going to be doing more personal debt borrowing. If I’m going to borrow, it will probably be more through SBA loans...I stress test the numbers.” — Jay

8. Future Plans and Enoughness

• Plans to continue expanding in car washes or possibly storage units.
• Considering building car washes from the ground up and possibly starting an accredited investor fund.
• No “life number”—prefers to stay engaged and active as long as it doesn’t encroach on family time.

Quote [12:44]:

“I have enough now that in cash flow and income that I could probably sit back...But I think I would get bored at home...my kids are younger and I do want to spend more time with them. So I kind of weigh a lot of the decisions I go forward based on, like, how much time does this take now?” — Jay

9. Reflection on Medicine vs. Entrepreneurship

• No regrets about choosing medicine; sees transferable skills from medical training applied to business.
• Emphasizes that doctors are capable of more than just their clinical identity and possess valuable, broad skillsets.

Quote [13:54]:

“I just don’t want to be identified as just a doctor...I think a lot of physicians identify only as that when you’re probably capable of a lot more...you pick up a very wide range of, like, skill sets that makes you very formidable in any arena that you step into.” — Jay

10. Advice for Aspiring Physician-Entrepreneurs

• You don’t have to be an entrepreneur, but everyone needs to know how to manage money efficiently to gain life flexibility and avoid burnout.
• Advocates self-education: “You owe it to yourself to sit down and study probably at least a good hundred hours” on money, investing, and modern finance trends.
• Encourages leveraging the abundance of free educational resources and seeking expert input.

Quote [16:37]:

“You’re going to spend like 20,000 to 40,000 hours of your life just working for money. And you owe it to yourself to sit down and study money and study investing and study all sorts of aspects...you can make the right moves for you in the future.” — Jay

11. Dr. Dahle’s Commentary: Three Pathways to Wealth (18:48–22:37)

• 1. Classic Path: High-income profession, invest 20% in index funds over 20–30 years. Slow but reliable.
• 2. Real Estate Path: Building a portfolio of short-term rentals—faster, requires learning, more risk, but reproducible.
• 3. Entrepreneurial Path: Fastest but least guaranteed; requires risk, hustle, and identifying new opportunities. “For those willing to take risks and hustle, it can pay off spectacularly—though it's not for everyone.”

Tax Loss Harvesting 101 (22:38–26:47)

Key Points & Practical Takeaways

• Definition: Tax loss harvesting is the process of selling a losing investment and purchasing a similar (but not “substantially identical”) security to book a loss for tax purposes—without significantly changing your portfolio.
• Examples: Swapping from a total stock market index fund to an S&P 500 fund.
• Tax Benefits:
  • Offset $3,000/year of ordinary income.
  • Offset unlimited capital gains.
  • Unused losses carry forward indefinitely (“schedule D”).
• Rules and Warnings:
  • “Wash sale” rule: Cannot rebuy the same or substantially identical security within 30 days, or the loss is disallowed.
  • Don’t “screw up” the trades—could lose value or the tax benefit.
  • Tax loss harvesting too frequently can convert qualified dividends to non-qualified (higher tax rate)—another reason to avoid excessive trading.

Quote [24:44]:

“Tax loss harvesting is not changing your portfolio, but still getting the loss...you book that loss, and what can you use the loss for? Well, you can use $3,000 a year of it against your ordinary income, and you can use an unlimited amount of that loss against capital gains.” — Dr. Jim Dahle

Notable Quotes & Memorable Moments

• On pursuing money mastery:
  [16:37] Jay: “You owe it to yourself to sit down and study probably at least a good hundred hours because then you can make the right moves for you in the future...”

• On financial freedom:
  [15:09] Jay: “You have to manage your own money and your own investments, otherwise you will be working for someone else...I don’t think that you necessarily...have to be entrepreneurial, but you should know how to manage your money.”

• On physician skillsets:
  [13:54] Jay: “...you have, like, really great communication skills. You probably negotiate all the time...you just got to bring them out and just apply them to...different areas of your life that you feel passionate about.”

Important Timestamps

• [01:44] – Jay’s Background
• [03:15] – Net Worth Breakdown
• [06:04] – Student Loan and Early Leverage
• [08:58] – Pivot to Business Ownership and Car Washes
• [11:01] – Risk Management and Debt Attitude
• [12:44] – Thoughts on “Enough” and Balancing Family
• [13:54] – Reflection on Medicine vs. Entrepreneurship
• [16:37] – Advice for Physicians Interested in Entrepreneurship
• [18:48] – Dr. Dahle’s Commentary: Three Pathways to Wealth
• [22:38] – Tax Loss Harvesting Primer

Takeaways for Listeners

• Career paths are diverse even for high-income professionals: Jay’s journey from hospitalist to car wash magnate exemplifies what’s possible with risk-tolerance, hustle, and lifelong learning.
• Self-education is non-negotiable: Even if you don’t want to run a business, you need to master financial basics to achieve independence.
• Leverage can be a tool—not just a risk: Used strategically and with contingency planning, it can rapidly accelerate wealth-building.
• Tax loss harvesting is a power move for high-income investors: Know the rules to optimize your investments without unnecessary risk or IRS trouble.

For physicians and similar professionals, this episode is a testament to the power of controlled risk, the value of being “your own CEO,” and the necessity of financial literacy—closing, as always, with Dr. Dahle’s signature encouragement to own your financial journey.