The Success Architect

Former Navy SEAL Chris Forrest joins Jake to talk about what it really takes to lead and motivate people. Chris shares how a “life resume” exercise led him to the SEAL teams, how he made it through BUD/S after starting over with a stress fracture, and how seminary, CIA contract work, and years of teaching led him to found TACTIC in Bozeman.

From there, they get into why Chris now focuses on being useful instead of just successful, and why vision is only 1% of the work while alignment is the other 99%. Chris breaks down how to get real buy-in from a team, why incentives have to match the message, how to handle holdouts, and why grinding it out isn’t sustainable without a bigger why.

Plus, Chris shares the one sentence he hopes ends up on his tombstone.

Momentum hit eight figures in three years, and then it stopped growing. Jake spent a long time looking for the reason before realizing the ceiling was him.

In this episode, Jake gets honest about how the same habits that build a company can end up capping it. He talks about the founder’s instinct to fill every hole, why “it’s faster if I just do it” works until it doesn’t, and the uncomfortable truth that the person who loves putting out fires has a quiet interest in the fires continuing.

He also walks through the practical side: using EOS/Traction accountability charts, building roles before names, and why a wrong name in a seat is worse than an empty one. Whether you’re a founder, a division leader, or anyone who’s become the go-to person for everything, this one is about learning to step out of the way and let your team actually lead.

Stop working to be needed. Start working to be worth having.

Jake Lewendal was twenty-six years old when an employee sat him down and told him something no one else ever had: he didn't do what he said he was going to do. And the employee was right. In this episode, Jake goes back to that moment — a career conversation on a bar patio that turned into the most honest feedback he'd ever received — and traces how a habit of overpromising quietly ran through his whole life, not just his business.

Jake doesn't soften it. He admits he made promises to employees and friends because it felt good to say yes in the moment, then let something else "come up" every time. He's candid about the version of the story that would look better — that he was making noble sacrifices for a growing company — and rejects it outright: at the time, he was simply on the grind, and he refuses to backdate a better excuse than the one that's true.

The episode turns from confession to method: how a self-described people-pleaser actually broke the habit — not through willpower or a moment of revelation, but through logistics. Jake explains how he learned to let his calendar say no for him until the reps built the character shift he couldn't will into existence.

What started as a hard truth from a young employee became a pillar of how Jake runs his company today: do what you say you're going to do. He closes by returning to that moment on the patio — and the realization that the one person who told him the truth almost certainly wasn't the only one who'd noticed.

Jake starts with a line from Justin Owens (New Age CEO) that stopped him cold: you can be a lion in public and a lamb in your own living room. 

In this episode, Jake takes that idea somewhere different — not disagreeing with it, but digging into why it happens, and what most men do wrong once they notice it.

Jake walks through his own five-thirty homecoming — frazzled, untransitioned, watching his kids gravitate toward his wife because he wasn't present enough to help them land — and traces it back to a bigger truth: home runs on a completely different feedback loop than work. At work, obligation turns into confidence fast — you solve something, you see the win. At home, you can lead well for three years and get no signal at all, until one ordinary dinner tells you it worked.

He's honest about the trap that follows: it's not that men choose to check out at home, it's that they never commit to a version of themselves that fits there. So they hover — half in, waiting to see which guy is needed tonight — and call it neutral, when it's really just leadership going missing in a different room.

The episode lands on a question Jake hasn't answered: how do you lead with peace, walking into a home that's already working without you, without wrecking what's already there? He doesn't wrap it in a bow. He leaves it open, because he'd rather ask the honest question than hand over a tidy answer that isn't true yet.

In this episode of The Success Architect, Jake sits down with Jeffrey Greenberg, founder and managing partner of Heritage, whose portfolio spans over 10 million square feet of flex, industrial, and office space from New Jersey to Montana, plus more than 7,000 multi-family units across Virginia and the Carolinas. Jeff has been a key player in Newark, New Jersey's revitalization since 2000, redeveloping over 800,000 square feet of downtown office space and earning Heritage two Building of the Year awards from BOMA.

But this conversation goes beyond the deals. With a philosophy degree from Colgate, a law degree from Boston University, and a master's in real estate from NYU, Jeff brings a rare, first-principles lens to how he thinks about risk, money, and life. He and Jake dig into why Jeff sees risk as an art rather than a science, the deathbed advice from his father that changed his approach to risk forever, and why he considers real estate to be one of the least risky investments out there.

The conversation also explores Jeff's ideas on "renting money and renting time," the power of compounding illustrated through the classic Chinese farmer parable, and his belief that money is a tool for freedom and impact, not an end goal. Jeff and Jake close out with a discussion on holistic living, why Jeff rejects the idea of "balance," and what it really means to compound every part of your life, not just your bank account.

A must-listen for anyone who wants to rethink risk, money, and what a well-built life actually looks like.

In the final episode of this series, Jake Lewendal helps listeners turn everything they've uncovered into something concrete: a short, written financial philosophy they actually own. After tracing where their money beliefs came from, learning to shift between scarcity and abundance on purpose, and reconnecting money to values instead of identity, Jake makes the case that a philosophy nobody writes down isn't really a philosophy — it's just a mood that shifts with stress.

He walks through four questions that define a real financial philosophy: what money is actually for, what risk posture fits your own season of life or business, what you protect no matter what, and what you're willing to be uncomfortable for. From there, Jake pushes listeners to write it down — and keep it short. A real philosophy fits on an index card, not a manifesto, and he offers a simple fill-in-the-blank structure to get started.

The episode closes by showing how to make that philosophy load-bearing: running real decisions — hires, purchases, investments, price increases — through it before acting, so it speeds up decision-making and cuts through inherited noise instead of sitting as inspirational wall art. For builders and business owners, Jake connects this directly to margin decisions, hiring timing, and scaling without breaking.

Jake leaves listeners with a challenge: write one paragraph this week, then test it on the next decision that comes up. As he puts it, the goal was never to hand anyone a philosophy — it was to make sure the one they're living by is actually theirs.

In this episode, Jake talks about why net worth and self-worth get tangled up so easily and what it actually takes to untangle them.

We've all met someone who lets their bank account do the talking - for better or worse. Here's the thing Jake has come to believe: money doesn't change who you are, it magnifies it. If you're generous, more money makes you more generous. If you're something else... well, you know how that plays out. It's not a wealth problem. It's a character problem wearing a wealth costume.

Jake breaks down the difference between using money as a means to build the life you want versus letting it define who you are in the room. He talks about the quiet ways status creeps into decision-making, why more zeros rarely solve the identity question, and how the most grounded high-performers he knows think about wealth differently than everyone assumes.

If you've ever caught yourself measuring your value by your numbers, this one's for you.

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In episode two of his money series, Jake Lewendal explores how our mindset around money shapes nearly everything else — how we live, work, invest, build businesses, and prepare for the future. Most of us swing between scarcity and abundance in how we relate to money, often without realizing it. In this episode, Jake breaks down how shifting toward a positive money mindset can change the trajectory of your decisions and outcomes.

Money is a tool — and how we use it either propels us forward or holds us back. But the real work isn't just about how much you make, it's about what you choose to spend it on. That's where scarcity and abundance thinking actually take root. Tune in for a grounded look at rewiring the way you think about money.

Most of us never chose how we think about money. We inherited it. In this episode, Jake breaks down where our financial habits actually come from: the beliefs about spending, saving, and investing that got wired into us long before we ever earned a paycheck.

Jake unpacks the concept of "money scripts," the unconscious rules formed by childhood experiences, family dynamics, and even one-off moments that quietly shape how we handle money as adults. Whether you're a saver, a spender, an avoider, or somewhere in between, this episode will help you spot the patterns running in the background and start making money decisions that are actually yours.

In this episode:

• Where our core beliefs about money come from
• Why money scripts drive behavior more than logic does
• How past experiences (even ones we don't remember) shape spending and saving habits
• The first step to rewriting an unhelpful money story

Most business owners are mixing their personal and business finances without even realizing the damage it's doing. In this episode, I sit down with Sarah Hurlburt, a financial expert with over 25 years of experience as a Controller, Tax Advisor, and Auditor, to talk about what it actually takes to build a business budget that works.

Sarah has spent her career helping small business owners get their financial house in order, across industries like restaurants, medical offices, construction, and professional services. We dig into why keeping your business and personal accounts separate isn't just good practice, it's foundational to understanding whether your business is actually profitable. We also talk about the financial blind spots that trip up even experienced owners, and the simple systems that make budgeting less overwhelming and more useful.

If you've ever looked at your bank account and had no idea what your business actually made last month, this episode is for you.