Bet on the Jockey: Why a Great “Deal” Doesn’t Guarantee Returns | Ep. 19

The Sage Principles That Scaled Sunrise Capital to $400M+ AUM | Ep. 23

A decade ago, Kevin Bupp and I ran Sunrise Capital Investors as a lean lifestyle business. There were no huge teams, global workforces, or hundreds of millions in assets under management. It was Kevin and I, finding deals, closing, integrating, and repeating, with some family and friends along the way. Now, in 2026, we manage over $400M in assets. No capital calls. Zero principal loss. Close to a decade of uninterrupted, on-time distributions. This wasn’t from luck, buying at the bottom, or taking advantage of low rates in 2020. This was achieved through disciplined investing and Sage principles, which took us to nearly the half a billion dollar mark. Today, Kevin is on to help me wind back the clock and share the story of how we did it. We’re going through all the lessons: How we went from a lifestyle company to an income-producing engine with a global workforce, the core value that’s made the ride so worth it, how our fund structure evolved to get investors the highest true return, and how we made it through the pandemic, interest rate shocks, and learned a new asset class we knew nothing about that in turn made our investors millions.  Sage Wisdom from Today’s Episode:  * How we scaled from a small lifestyle company to a $400M+ AUM business  * Why outsourcing the wrong things as you grow can slow you down, not speed you up  * Making your way through “the fog” when running a small (but quickly scaling) business  * The principles that allowed us to buy, while our competitors were stuck on the sidelines  * The mom-and-pop asset class still years behind other industries that we’re doubling down on  * How our fund structure evolved to give investors the greatest benefits possible — Invest with Sunrise Capital [https://sunrisecapitalinvestors.com/register-for-the-deal-room/] Listen to Kevin’s Podcast, Real Estate Investing for Cash Flow [https://kevinbupp.com/podcast/] Connect with Kevin on LinkedIn  [https://www.linkedin.com/in/kevinbupp] Lessons That Took Me from a Mobile Home to Millionaire | Ep. 3 [https://brianspear.com/lessons-that-took-me-from-a-mobile-home-to-millionaire-ep-3/] Recommended Resources: * Learn more from Brian [https://brianspear.com/] and listen to past episodes of The Sage Investor  * Connect with Brian [https://www.linkedin.com/in/brian--spear] on LinkedIn Are you a high net worth investor with capital to deploy in the next 12 months?Build passive income and wealth [https://sunrisecapitalinvestors.com/register-for-the-deal-room/] by investing in real estate projects alongside Brian and his team! 00:00 Intro 01:33 The V1 of Sunrise Capital 04:39 Becoming a True Business 07:36 Enjoy the Ride! 09:49 The "Fund" Evolution 14:31 The "Massive Shift" We Needed to Make 19:38 Growing Fast...Pandemic Hits 25:12 Remote Hiring Changed Everything 27:37 Moving Through "The Fog" 29:15 The "Buying Spree" Begins 35:03 A Massively Underrated Asset 41:46 Surviving the Interest Rate Shock 56:22 Next Goal? $1B AUM. 58:29 Kevin's Sage Principle

Living Abroad in His 40s, Funded by Passive Cash Flow | Ep. 22

This is what financial freedom looks like. Within a matter of months, Adam Cranmer is packing up his family and moving abroad to Spain—not for a few weeks, but for good. His goal of expanding his son’s worldview is becoming reality, and Adam’s life of European travel, slow days, and savoring Spanish wine has only just begun—and it’s being funded by passive cash flow. When most people think of financial freedom, they think of a pile of money, enough to stop them from worrying—but Adam is thinking of it another way. Will my investments produce steady, durable cash flow that can cover my family—even when work stops? In this episode, Adam shares his wisdom from over a decade of battle-tested investing, how he grew a sizable active portfolio, became an LP, and eventually switched from aggressive acquirer to Sage steward of his family’s wealth. He’s hit his financial freedom goal and shares the pitfalls that could have delayed his journey as a passive investor by years if he had listened to all the noise from speculators. Adam’s life may seem like a dream, but for many passive investors, it’s closer to reality than they think.  Sage Wisdom from Today’s Episode:  * How Adam, only in his 40s, is already living the life most investors dream of  * The different levels of financial freedom and the one that will secure you a worry-free future * Why the shift from accumulation to stewardship is the most important move a Sage investor makes * How the operator, not the deal, gives investors peace of mind and real passive income  * Mistakes passive investors make and easily fall into that will lose them money, and delay their freedom * Why the wealth you build today is really about the worldview you give your children tomorrow — Connect with Adam on LinkedIn [https://www.linkedin.com/in/adamcranmer] Bet on the Jockey: Why a Great “Deal” Doesn’t Guarantee Returns  | EP. 19 [https://brianspear.com/bet-on-the-jockey-why-a-great-deal-doesnt-guarantee-returns-ep-19/] Recommended Resources: * Learn more from Brian [https://brianspear.com/] and listen to past episodes of The Sage Investor  * Connect with Brian [https://www.linkedin.com/in/brian--spear] on LinkedIn * Are you a high net worth investor with capital to deploy in the next 12 months? Build passive income and wealth [https://sunrisecapitalinvestors.com/register-for-the-deal-room/] by investing in real estate projects alongside Brian and his team!  00:00 Intro 01:32 You've Built Wealth, Now Keep It 05:17 THIS Is Financial Freedom 11:16 Passive Investors Get This Wrong 21:04 What Adam's Investing in Now 28:53 Giving Your Kids a Fuller Life 37:53 The Perfect Day 41:33 Adam's Sage Principle 44:16 Invest in Your Dream Life

You Don't Need More Deals: Get Higher Returns From What You Already Own | Ep. 21

Most wealthy investors don’t need more deals—they need to structure deals more intelligently to survive taxes. Imagine keeping the same portfolio and getting higher after-tax returns without gimmicks, risky tax strategies, or chasing every deduction.  It’s more than possible if you’ve got the right real estate tax strategy.  Today, we’re welcoming our first guest to The Sage Investor podcast, Kim Lochridge, EVP of Engineered Tax Services [https://engineeredtaxservices.com/]. Kim has personally helped me and our investors save substantial sums in taxes by doing what most average CPAs overlook.  We’re going deep on something beyond depreciation, beyond the short-term rental tax loophole—partial asset disposition. Unlike some deductions, partial asset disposition is a one-time opportunity—once the window closes, it's gone permanently. And passive investors, you aren’t counted out of this. These paper losses can lead to sizable passive losses on your taxes, which could benefit your other investments or properties.  Kim unlocks one of the most overlooked tax benefits available to real estate investors, and shares her Sage Principle that every investor needs to hear before signing their tax returns. Sage Wisdom from Today’s Episode:   * How partial asset disposition supercharges your tax benefits far beyond regular depreciation  * What investors must do before 2027 if they’re investing in one specific tax-advantaged asset * Why depreciation recapture is much less severe (and much more avoidable) than you think * How passive investors can use paper losses to offset other income streams   * The two tax “strategies” that (often) aren’t worth the effort  — Connect with Kim on LinkedIn [https://www.linkedin.com/in/kim-lochridge-74b21619/] Engineered Tax Services [https://engineeredtaxservices.com/] Recommended Resources: * Learn more from Brian [https://brianspear.com/] and listen to past episodes of The Sage Investor  * Connect with Brian [https://www.linkedin.com/in/brian--spear] on LinkedIn * Are you a high net worth investor with capital to deploy in the next 12 months? Build passive income and wealth [https://sunrisecapitalinvestors.com/register-for-the-deal-room/] by investing in real estate projects alongside Brian and his team!  00:00 Intro 03:10 Pay Less on Your CURRENT Portfolio 06:06 Do This Before 2027 07:42 Greater Than Depreciation? (Partial Asset Disposition) 15:48 You're Wrong About "Recapture" 18:05 Every Investor Should Do This 22:39 Paper Losses for Passive Investors 27:58 Dangerous Tax "Strategies" 31:29 Kim's Sage Principle 34:43 Connect with Kim!

The Nest Egg Lie: Why Most Retirement Plans Fail (And What to Do Instead) | Ep. 20

Many investors spend their entire life building wealth, amassing a sizable nest egg, on the premise that it will fund their retirement, support their children, and give them the peace they’ve spent decades sacrificing for. This is a lie—and it’s why many Americans, even high-net-worth investors, are riddled with anxiety, sitting on a fragile foundation that won’t support their life the way they intended. The nest egg retirement withdrawal strategy you’ve been told to follow is more fragile than you think. There are two ways to retire: one that gives you peace of mind and ultimate life autonomy, and the other that keeps you worrying at night, wondering if your next withdrawal could be your last. This is the Sage Principle of the golden goose vs. the nest egg. Buying with forever in mind and owning durably wonderful assets vs. withdrawing until your account runs dry. And today, I’m explaining why one works, and the other is merely misinformed speculation hidden under the guise of smart retirement planning. The true question isn’t how do you invest enough to sustain yourself in retirement, the actual question worth solving is the cash flow riddle: How much passive income do you need coming in to give you ultimate optionality with the least stress possible? Here's how to take the first step toward replacing fragile withdrawals with durable cash flow. Sage Wisdom from Today’s Episode:  * Why nest egg retirement withdrawal strategies are much more fragile than you think * How to create a “golden goose” that produces durable cash flow while your net worth grows  * What are you chasing: more freedom or a bigger bank balance when you’re gone? * The “cash flow riddle” that, once solved, gives you access to your freest life  * Perform this exercise to find the true “freedom number” you truly need to live the life you want  — The Cash Flow “Riddle”: Solve It, and You’re Free for Life | Ep. 4 [https://brianspear.com/the-cash-flow-riddle-solve-it-and-youre-free-for-life-ep-4/] Recommended Resources: * Learn more from Brian [https://brianspear.com/] and listen to past episodes of The Sage Investor  * Connect with Brian [https://www.linkedin.com/in/brian--spear] on LinkedIn Are you a high net worth investor with capital to deploy in the next 12 months?Build passive income and wealth [https://sunrisecapitalinvestors.com/register-for-the-deal-room/] by investing in real estate projects alongside Brian and his team! 00:00 Intro 01:52 Freedom over Net Worth 03:36 Nest Egg vs. Golden Goose 09:01 This Changes Everything 13:57 How Long Will YOU Wait for Freedom? 18:12 Do This Before It's Too Late

Bet on the Jockey: Why a Great “Deal” Doesn’t Guarantee Returns | Ep. 19

Most limited partners spend hours analyzing the deal, the market, and the potential returns. They see a high IRR, growing demand for a property, and maybe even economic tailwinds. They put tens of thousands, if not hundreds of thousands, of dollars into the deal, assured that it would be a home run. Then months go by, distributions are paused, a capital call email lands, and the investors are wondering how much of their capital will be returned. The deal was great. The numbers were solid. Everything checked out. So what happened? They bet on the horse, not the jockey. At Sunrise Capital Investors [https://sunrisecapitalinvestors.com/], we believe in a Sage Principle: Bet on the jockey, not the horse. A deal can look great on paper, but if a “lucky” operator is running it during a bad market, all those projections go out the window. They get paid their fees, and you walk away with, sometimes, a significant loss of capital.  So, how do you spot a great real estate sponsor from a lucky one? Today, we’re diving into this principle in detail, including the three traits every great operator has, and the single most important one. Plus, what to ask every single operator before you invest to flag whether they’ll make it during a downturn or change in the cycle.  This doesn't just help you avoid the wrong operators. It helps you find the extraordinary ones. Sage Wisdom from Today’s Episode:  * Why it’s the operator (not the deal) that loses investor capital  * The one crucial trait that every great operator must have that lucky and average ones lack * How to evaluate whether your operator can navigate a downturn (ask every sponsor these questions) * How much of my own money I’ve put into our deals at Sunrise Capital Investors [https://sunrisecapitalinvestors.com/]  * Why the best operators look like fools during the biggest bull markets (they called Buffett an idiot) — Why Most Investors Misunderstand Risk | Ep. 14 [https://brianspear.com/why-investor-misunderstand-risk-ep-14/] Recommended Resources: * Learn more from Brian [https://brianspear.com/] and listen to past episodes of The Sage Investor  * Connect with Brian [https://www.linkedin.com/in/brian--spear] on LinkedIn * Are you a high net worth investor with capital to deploy in the next 12 months? Build passive income and wealth [https://sunrisecapitalinvestors.com/register-for-the-deal-room/] by investing in real estate projects alongside Brian and his team!  0:00 Intro 1:00 Sponsors (NOT the Deal) Lose Money 2:42 Bet on the Jockey 4:21 One Thing Great Operators Have 5:54 Revealing the Bad Operators 9:02 Ask Every Sponsor This 10:39 Have Skin in the Game 13:53 The REAL Problem