Wholesaling and buy-and-hold are not the same business—so why do so many investors track them the same way? In this episode, I break down how money actually flows differently between wholesaling, fix-and-flip, and buy-and-hold strategies, and why lumping everything into one set of numbers can quietly destroy your profits.

I walk through real examples of investors unknowingly using rental cash flow to prop up losing wholesale or flip operations, the legal and financial risks of mixing strategies, and exactly what you should be tracking for each model. If you’re using wholesaling as your cash engine and buy-and-hold as your long-term wealth play, this episode will help you stop guessing and start making intentional decisions with your money.

Timeline Highlights:

[0:00] Why wholesaling and buy-and-hold should never be tracked the same way

[1:21] The danger of lumping multiple strategies into one set of financials

[1:51] The legal and liability risks of mixing wholesale and rental operations

[2:56] Wholesale as a cash machine vs. buy-and-hold as a wealth builder

[3:35] A real example of rentals silently covering wholesale losses

[4:42] The three simplest numbers every strategy must track

[5:21] Why buy-and-hold profits don’t always match bank balances

[6:06] How Profit First brings clarity to both strategies

[7:35] What wholesalers must track to avoid reinvesting everything

[8:51] Marketing ROI vs. equity growth—what matters for each strategy

[10:30] Using strategy-specific tracking to escape the rat race

Key Takeaways

1. Wholesaling and buy-and-hold are fundamentally different businesses with different money flows.
2. Combining multiple strategies into one financial view creates blind spots and risk.
3. Wholesaling is primarily a cash and marketing business, not a wealth strategy.
4. Buy-and-hold success depends on true cash flow, debt service, and equity growth.
5. Rentals can silently subsidize losing wholesale or flip operations if not tracked separately.
6. Profit First helps clarify what you make, spend, and keep in each strategy.
7. Tracking the right numbers allows each strategy to stand on its own financially.

Links & Resources

Book a free discovery call and get help structuring your numbers by strategy: profitrei.com

Closing:

Thanks for spending time with me today. If this episode helped you see the difference between wholesaling and buy-and-hold more clearly, make sure to follow the show, leave a review, and share it with another investor who’s running multiple strategies. And if you’re ready to apply what we talked about with real guidance and accountability, visit profitrei.com and book your free discovery call to start building true financial clarity and freedom.

In this episode, I sit down with Aaron Letzeiser, co-founder of OB Insurance, to talk about one of the most overlooked (and overpaid) areas in real estate investing—insurance. If you’ve ever felt frustrated by rising premiums, confusing policies, or slow claims, this episode will be a game-changer.

Aaron shares why insurance is getting more expensive (especially in markets like Florida and Texas), what most investors get wrong about their coverage, and how OB is changing the way real estate pros manage risk. We dive into how OB uses tech to create fast, transparent quotes, the difference between replacement cost and actual cash value, and how to take back control of your costs—without sacrificing protection.

Episode Highlights

[0:00] – Introduction

[0:32] – Why insurance is one of the most misunderstood costs in real estate

[2:04] – Aaron’s background and how he went from private equity to co-founding OB

[4:20] – What OB Insurance does and how it’s built specifically for real estate investors

[7:39] – Why transparency and speed matter more than ever in today’s insurance market

[10:26] – Types of coverage OB offers: short-term flips, long-term rentals, and more

[13:14] – What’s really driving rising insurance costs—and how to mitigate them

[16:18] – How investors can reduce risk factors and potentially lower their premiums

[17:02] – The OB claims process and how it’s different from traditional carriers

[24:12] – Understanding replacement cost vs. actual cash value—and what you should choose

[28:55] – Final takeaways for protecting your portfolio while saving money

5 Key Takeaways

1. Insurance is often overpaid and under-optimized. Most investors don’t know how to evaluate policies, leaving money on the table.
2. OB puts investors in the driver’s seat. From fast digital quotes to customized coverage, the platform was built for real estate.
3. Your location is affecting your premium more than ever. Be proactive if you’re investing in storm-prone areas.
4. Know your valuation model. Replacement cost and actual cash value offer different protections—know which one you’re buying.
5. Claims don’t have to be painful. OB’s tech-forward claims process is designed to be fast, transparent, and easy to manage.

Links & Resources

• OB Insurance: https://www.obieinsurance.com
• Email Aaron: aaron@obieinsurance.com
• Learn more about Profit First for real estate investors: https://www.simplecfo.com

If this episode helped you rethink how you protect your real estate business, please rate, follow, and review the show. And don’t forget to share it with another investor who needs this kind of clarity.

If you can’t instantly see your numbers, you’re not really running a business—you’re rolling the dice. In this episode, I break down why so many real estate investors and entrepreneurs feel constant financial pressure even when deals are closing and money is coming in.

I walk through what true financial clarity actually looks like, why tracking the right numbers matters more than tracking all the numbers, and how cash-flow forecasting can help you make smarter decisions before problems show up. Whether you’re flipping, wholesaling, buying and holding, or running a multi-deal operation, this episode will help you stop reacting to your finances and start leading your business with confidence.

Timeline Highlights:

[0:00] Why running a business without clear numbers is like rolling the dice

[1:04] The real reason business owners make money but still feel stuck

[2:05] How cash crunches happen—and why they’re inevitable without systems

[3:05] The first number every business owner should be tracking

[4:06] How to measure marketing ROI using both money and time

[5:31] Why “work in progress” drains cash in real estate businesses

[6:29] Using dedicated accounts to track project cash and investor funds

[8:11] The key numbers every owner should see on a financial dashboard

[11:01] Why forecasting gives you a crystal ball for future decisions

[13:22] How financial clarity reduces stress and drives real freedom

Key Takeaways

1. Financial clarity means knowing where every dollar is going—and why.
2. Tracking numbers only matters if they help you make better decisions.
3. Marketing spend must be measured against real returns, not gut feelings.
4. Real estate investors must separate operating cash from project cash.
5. Cash-flow forecasting helps you plan for both best-case and worst-case scenarios.
6. A financial dashboard turns numbers into actionable insights.
7. Confidence in business comes from visibility, not just profitability.

Links & Resources

Book a free discovery call and get help building clarity and forecasting into your business: profitrei.com

Closing

Thanks for spending time with me today. If this episode gave you clarity or a new perspective, make sure to follow the show, leave a review, and share it with another investor or business owner who needs better visibility into their numbers. And if you’re ready to apply what we talked about with real guidance and accountability, visit profitrei.com and book your free discovery call to start building true financial clarity and confidence.