Profit First for Real Estate Investors with David Richter

In this episode, I sit down with business attorney Chris Johnsen, who brings a refreshingly honest take on when investors really need legal help—and when they don’t. With a background in real estate, litigation, and corporate counsel, Chris knows firsthand how legal blind spots can cost you big. But he also gets the hustle. He’s not here to sell legal services you don’t need—he’s here to help you think like a business owner.We dive into when to engage a lawyer (hint: not always day one), what contracts investors mess up the most, and the risks of using boilerplate docs or DIY operating agreements. Chris also tackles hot topics like non-competes, asset protection, and the legal lines you might be crossing without even realizing it—especially in syndications.Episode Highlights[0:00] – Chris shares his journey from real estate to law and why he’s a businessperson first[5:03] – How the 2008 crash redirected his path and made him a litigation expert[6:56] – The unexpected upside of being both a transactional and litigation attorney[9:25] – Why the “school vs. entrepreneurship” debate is missing the real question[12:40] – What makes a law degree valuable—and how to think about ROI in education[13:46] – Why cash is underrated, and how it gives you leverage in business and investing[15:11] – Real estate can create freedom—but it takes a lot more than just doors[17:16] – Most common legal issues investors bring to Chris’s firm[19:05] – Corporate structure and asset protection: the basics you must get right[21:06] – What’s happening with non-compete laws and why it matters to business owners[22:30] – DIY contracts, LegalZoom templates, and when it becomes a $20K problem[23:21] – Operating agreements: why they’re not just “boilerplate” documents[24:10] – Syndications and securities law: the big legal risk investors overlook[27:11] – The million-dollar mark: when you should really start investing in legal infrastructure[31:13] – How to connect with Chris and book a free 15-minute consult5 Key TakeawaysYou don’t need a lawyer for everything—but you better get the operating agreement right. It’s not just paperwork. It’s the contract that holds your business together.DIY legal is fine—until it’s not. Contracts, partner agreements, and syndications are where most investors go wrong.Forming an entity is simple. Scaling with structure isn’t. Corporate governance matters more as you grow.Syndications trigger securities laws. If you’re raising capital, you need a securities attorney—not just a real estate one.Once your business hits seven figures, legal issues multiply. That’s when it’s time to audit what you’ve built—and protect what you’ve earned.Links & ResourcesBook a free consult with Chris: https://www.johnsenlaw.comLearn more about Profit First for real estate investors: https://www.simplecfo.comIf this episode gave you clarity on how and when to protect your real estate business, make sure to rate, follow, and review the podcast. And share this with an investor who might be one contract away from a $20K mistake.

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 raceKey TakeawaysWholesaling and buy-and-hold are fundamentally different businesses with different money flows.Combining multiple strategies into one financial view creates blind spots and risk.Wholesaling is primarily a cash and marketing business, not a wealth strategy.Buy-and-hold success depends on true cash flow, debt service, and equity growth.Rentals can silently subsidize losing wholesale or flip operations if not tracked separately.Profit First helps clarify what you make, spend, and keep in each strategy.Tracking the right numbers allows each strategy to stand on its own financially.Links & ResourcesBook a free discovery call and get help structuring your numbers by strategy: profitrei.comClosing: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 money5 Key TakeawaysInsurance is often overpaid and under-optimized. Most investors don’t know how to evaluate policies, leaving money on the table.OB puts investors in the driver’s seat. From fast digital quotes to customized coverage, the platform was built for real estate.Your location is affecting your premium more than ever. Be proactive if you’re investing in storm-prone areas.Know your valuation model. Replacement cost and actual cash value offer different protections—know which one you’re buying.Claims don’t have to be painful. OB’s tech-forward claims process is designed to be fast, transparent, and easy to manage.Links & ResourcesOB Insurance: https://www.obieinsurance.comEmail Aaron: aaron@obieinsurance.comLearn more about Profit First for real estate investors: https://www.simplecfo.comIf 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 freedomKey TakeawaysFinancial clarity means knowing where every dollar is going—and why.Tracking numbers only matters if they help you make better decisions.Marketing spend must be measured against real returns, not gut feelings.Real estate investors must separate operating cash from project cash.Cash-flow forecasting helps you plan for both best-case and worst-case scenarios.A financial dashboard turns numbers into actionable insights.Confidence in business comes from visibility, not just profitability.Links & ResourcesBook a free discovery call and get help building clarity and forecasting into your business: profitrei.comClosingThanks 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.

In this episode of the Profit First for Real Estate Investing podcast, I sit down with Dave Dupuis, one-half of the dynamic duo behind Investor Mel & Dave. Dave shares how he and his wife Mel built a thriving real estate business—owning over 250 units across five countries—without ever using joint venture partners. From his early days as a firefighter to scaling their portfolio through creative financing, Dave unpacks the mindset shifts, systems, and strategies that helped them achieve financial freedom and teach thousands of others to do the same.We get into the nuts and bolts of using other people’s money the right way, how to protect your equity while growing fast, and the power of not giving up decision-making control. Dave also opens up about how a life-threatening car accident led them to start coaching and why keeping your business aligned with your values is the key to long-term success.Episode Highlights[0:00] - From firefighter to full-time real estate investor: Dave’s unexpected journey[1:44] - The secret to working successfully with your spouse[2:43] - Why they left their jobs to go all-in on real estate[5:04] - The “aha” moment that changed everything for Dave[7:35] - How they bought 12 properties in 12 months using creative financing[9:20] - The near-fatal accident that sparked a shift to coaching[11:05] - Over 2,000 students and counting: What makes their program different[12:28] - Why Dave refuses to do joint ventures—and what he does instead[15:31] - Their approach to multifamily and why they still invest in small properties[16:29] - The three creative financing strategies they use (and teach)[18:18] - How real estate helps them support their family goals[21:06] - Why they brought on Simple CFO and how it’s improved their decision-making[22:38] - Inside their coaching model and what students can expect[25:08] - What Dave would do differently if starting over today[27:03] - Final advice for stabilizing and growing your real estate businessKey TakeawaysCreative financing is key: You don’t need JVs—using OPM through seller financing, promissory notes, and retirement funds can scale your portfolio without giving up control.Keep the decision-making power: Dave explains how avoiding JVs allows him and Mel to make financial decisions aligned with their family goals.Stabilization > growth: Long-term success means periodically slowing down to strengthen your foundation before scaling again.The right systems matter: Bringing in financial pros like Simple CFO gave them the clarity and time to focus on growth.Serve from experience: Their coaching model is built on what they wish they had when starting—actionable, honest, and fully aligned with what they practice.Links & ResourcesConnect with Dave & Mel: https://www.instagram.com/investormelanddaveLearn more or book a call: https://www.investormeldave.comBonus for Profit First listeners: Visit https://www.investormeldave.com and mention “Simple CFO” for exclusive accessLearn more about Simple CFO: https://www.simplecfo.comIf this episode gave you valuable insights, please follow, rate, and review the podcast. And don’t forget to share it with a fellow investor who needs to hear this message today!

Book your FREE financial discovery call at ProfitREI.comIf your business is profitable on paper but your bank account tells a completely different story, this episode is for you. I hear this all the time—business owners doing great revenue, being told by their CPA that they’re profitable, yet still feeling broke, stressed, and unsure where the money is actually going.In this episode, I break down why this disconnect happens and why it’s almost never a revenue problem—it’s a system problem. I share real conversations with business owners, lessons from my own entrepreneurial journey, and how implementing a simple framework like Profit First can completely change how you experience money in your business—without spreadsheets, accounting jargon, or overwhelm.Timeline Highlights:[0:00] Why so many profitable businesses still feel broke and financially stressed[1:04] The frustration of doing all the work but not getting to keep the money[2:30] My personal experience running high-revenue businesses with no financial clarity[3:17] How discovering Profit First changed the way I looked at money forever[4:18] A real client story of digging out of the hole by fixing cash flow first[6:07] Why entrepreneurs struggle with numbers—and why that doesn’t have to stop you[7:08] The “Golden Trio” of bank accounts that helps you finally keep what you makeKey Takeaways: Profit doesn’t matter if you never actually see it in your bank account. Most entrepreneurs don’t have a money problem—they have a money system problem. Revenue alone won’t create financial freedom without intentional allocation. You don’t need to love spreadsheets to understand and control your numbers. Separating money into purpose-driven bank accounts creates clarity and control. Keeping profit, paying yourself, and planning for taxes must happen first, not last.Links & Resources:Schedule a free discovery call and get guidance on implementing Profit First: profitre.comClosingThanks 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 business owner who’s working hard but still feels broke. And if you’re ready to apply what we talked about with real guidance and accountability, head over to profitre.com and book a free discovery call to start building your path to financial clarity and freedom.

In this episode, I sit down with Martine Richardson—real estate investor, educator, and freedom advocate—to break down the real numbers behind getting out of the rat race. Martine’s story isn’t just inspiring, it’s filled with tactical advice for anyone who’s trying to create true financial freedom through real estate. From getting her car repossessed to building a portfolio that bought back her time, Martine shares how she leveraged creative financing, community, and consistency to scale her business.We talk about the real math behind financial freedom, how different rental strategies stack up (short, mid, and long-term), and why she’d go straight to buy-and-hold if she were starting over today. If you’ve ever asked yourself “how many doors is enough?”, Martine gives you a simple framework to find your freedom number.Timeline Summary:[0:00] - Martine shares how getting fired and losing her car kickstarted her real estate journey[5:40] - Her first creative deal: a lease option that changed her mindset[8:09] - How that $35K house turned into a $240K asset—and how she structured the deal[9:17] - Why meetups and podcasts were essential to her early success[11:12] - The shift from wholesaling to buy-and-hold—and using other people’s money[14:18] - What is a “freedom number” and how to calculate yours[18:24] - Comparing cash flow between long-term vs. mid-term rentals[22:25] - How fewer mid-term properties can replace your job income[25:48] - Would she still wholesale if starting over today? Her answer might surprise you[29:00] - Action over analysis: her advice for anyone stuck in “learning mode”5 Key Takeaways:Creative financing is key – Martine’s first deal came from asking sellers if they’d take payments. One finally said yes, and it changed everything.Community is a shortcut – Meetups, podcasts, and mentors gave her the knowledge and confidence to keep going, even when deals were slow.Buy-and-hold builds real wealth – Her accidental landlord story turned into a multi-property portfolio that now funds her life.Know your “freedom number” – She walks you through how to calculate exactly how many properties you need to quit your job, depending on cash flow type.Short, mid, or long-term? – Each rental strategy has trade-offs in risk and reward. Martine shares how she balances all three.Links & Resources:Text Martine for coaching or questions: 804-495-1333Learn more about Profit First for REI: https://www.simplecfo.comIf this episode gave you clarity, confidence, or a new way to think about financial freedom, please rate, follow, and review the show. And share it with another investor who needs to hear Martine’s story.

In this episode, I sit down with Frank Iglesias—a real estate investor, coach, and host of the What Worked for You podcast—to unpack the journey from chaos to clarity. Frank opens up about how burnout from his IT job led him to real estate, but also how the entrepreneurial learning curve nearly burned him out all over again.We dive into the pitfalls of trying to do too many things at once, why real estate investing is only one part of the business equation, and how Profit First helped him regain control of his finances. Frank shares the hard lessons of jumping into new construction too early, the value of having a business coach, and why mastering the fundamentals is the only way to scale sustainably.Episode Highlights[0:00] – Introduction[2:32] – From IT burnout to a Rich Dad seminar and the first taste of real estate[5:10] – How trying too many strategies at once slowed his growth[6:14] – The difference between learning real estate and learning business[6:33] – The pivotal role a business coach played in aligning his operations[9:18] – Why bookkeeping is the most underrated skill in real estate investing[14:06] – Lessons learned from jumping into new construction without the right model[22:57] – The risk of cheap lots and the hidden costs of building ground-up[25:19] – The reality of delayed income and managing cash flow in big projects[27:03] – Avoiding shiny object syndrome and returning to core business principles[30:54] – How to connect with Frank and learn more about his podcast and mentorship5 Key TakeawaysFocus is your fastest path to success. Early on, avoid chasing multiple strategies—go deep, not wide.Business fundamentals matter more than tactics. Learn how to manage money, lead people, and build systems.A coach can connect the dots. Frank’s biggest business breakthroughs came after investing in the right mentor.New construction is not a beginner strategy. It has different timelines, risks, and financial realities.You don’t need more books—you need to implement. Information is everywhere, but application is what creates results.Links & ResourcesVisit Frank online: https://www.frankiglesias.comCall or text Frank directly: (678) 408-2228Listen to Frank’s podcast: What Worked for YouLearn more about Profit First for real estate investors: https://www.simplecfo.comIf this episode helped bring clarity to your investing journey, please rate, follow, and review the show. And share it with someone else who’s ready to stop guessing and start building a real business.

In this episode, I sit down with Jason Lavender—a real estate investor and former painting contractor—who gets real about his rocky relationship with money and how Profit First finally changed his life. Jason shares the painful truth about how he ran his business by looking at his bank balance, faced constant stress despite making money, and ignored the warning signs until everything boiled over.What makes this episode so powerful is Jason’s honesty. He didn’t get it right the first—or even the second—time he tried Profit First. But when he finally committed, delegated implementation, and surrendered access to his own money, everything shifted. We talk about how he transitioned from a chaotic hustle into a clear, structured, and profitable business, and how you can too.Episode Highlights[0:00] – Jason’s early years as a painting contractor and the shift to real estate investing[2:59] – The stress and confusion of “bank balance accounting”[4:35] – How Profit First didn’t stick the first two times—and what made it click the third time[5:33] – The critical moment: giving financial control to his assistant (his daughter!)[8:44] – Going all in on real estate—and leaving the painting business behind[10:00] – “Burning the ships” and betting everything on building his investment business[11:28] – Regret and hindsight: How Profit First could’ve helped during his business exit[14:07] – The turning point question: “Where did all the money go?”[17:25] – Building a real business, not just a hustle—and the peace that came with it[21:06] – What a healthy business looks like for Jason today: structure, clarity, protection[24:07] – The role of coaching and audits in getting brutally honest with the numbers[29:19] – Final advice for investors stuck in the financial fog5 Key TakeawaysFalse starts are part of the process. Jason didn’t get Profit First right until he let go of control and got help.Delegating finances can be your superpower. Hiring his daughter to manage the system changed everything.Profit First brings peace. It gave Jason clarity, confidence, and control over his money and decisions.You can’t fix what you won’t face. Financial audits and coaching helped Jason confront what wasn’t working.There’s no shame in getting help. Real transformation happened when Jason stopped trying to do it all alone.Links & ResourcesFollow Jason on Facebook: https://www.facebook.com/jason.lavender.787084Check out Elevate Mentoring: https://elevatementoring.coachNeed help implementing Profit First? Book a call: https://www.simplecfo.comIf this episode hit home, don’t forget to rate, follow, and review the show. And share it with someone who’s tired of the hustle and ready to get financially healthy—for good.

In this powerful episode, I sit down with my long-time friend and serial entrepreneur Eddie Wilson—widely known as the “King of Exits”—to unpack what it truly means to build with purpose. Eddie shares how he has successfully exited over 113 companies and why his mission extends far beyond business. From navigating his first accidental exit to building a global nonprofit impacting 108 countries, Eddie walks us through how purpose, fulfillment, and systems of leadership have shaped his entrepreneurial path.We also dive deep into his real estate journey, how he integrates tax strategy and endowments, and why legacy means creating something that can thrive without placing a burden on the next generation. Whether you’re a real estate investor, business owner, or mission-driven leader, this episode will challenge your definition of success and ignite a deeper sense of intentionality in your work.Episode Highlights[0:00] - Eddie’s entrepreneurial journey from his early 20s to now overseeing 113 business exits[2:23] - Why fulfillment never comes at the end of the dollar and how purpose drives Eddie’s business philosophy[3:34] - The true meaning of legacy and why Eddie is focused on endowing his nonprofit[5:08] - Real estate as a generational vehicle: transitioning from flashy purchases to long-term passive income[6:56] - Using multifamily investing as a tax strategy and tool for perpetuity[8:04] - Eddie’s first “accidental” business exit and the life-changing lessons he learned[11:59] - Realizing how buying and selling companies can help “redeem time” and fast-track your 80-year-old life[14:06] - The business of leadership: what it takes to go from managing yourself to leading leaders[16:20] - Building the Empire Operating System used by 3,000 companies globally[18:09] - The two critical attributes of a leader of leaders: conscious competence and mitigating personal weaknesses[21:11] - Why people—not marketing, finance, or strategy—are the hardest and most important part of business[24:09] - Can leadership be taught or is it innate? Eddie’s answer may surprise you[27:10] - A powerful example of leadership legacy through Nick Saban’s coaching tree[28:00] - How to connect with Eddie Wilson and tap into his ecosystem of purpose-driven ventures5 Key TakeawaysLegacy Isn’t Just Purpose—It’s Sustainability: Eddie’s goal isn’t just to create impact but to ensure it lives on without being a burden to the next generation.Real Estate Is a Long-Term Wealth Vehicle: From tax strategy to endowment planning, real estate played a crucial role in Eddie’s financial architecture.Your First Exit Could Change Everything: Eddie’s accidental exit taught him the power of exponential value and redeeming time.Leadership Is a Learnable Pattern: Through his book Titan Leadership and the Empire Operating System, Eddie shows how great leaders are built, not born.People Are the Greatest Variable: Business success hinges on how well you lead and manage people—systems matter, but people matter more.Links & ResourcesCollective Influence – Eddie’s private equity firm: https://collectiveinfluence.comImpact Others – Learn more about Eddie’s global nonprofit: https://impactothers.comFollow Eddie Wilson on Instagram: https://www.instagram.com/eddiewilsonofficialSimple CFO – Get help with cash flow and profitability: https://simplecfo.com