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2015 Chicago Marathon. Mile 13. I’m flying—feeling like I could run forever. Heart surgery, back surgery, barely able to stand a decade before, and here I am crushing it. Then I see the sign: NOT ALMOST THERE. Everything changed. Heavy legs. Cramping. Mental breakdown. I barely finished what started as my best race ever. That sign broke me, but it also built me. Southside Chicago kid who studied for 15 seconds between building cars on the assembly line. Graduated in 5 years. Built companies. Sold two. 800 employees. Young father at 20 who figured it out as I went. I’ve spent 50+ episodes of Not Almost There interviewing experts, and now my cohost and I are diving deeper into the conversations that matter most. We dig into what it really takes—in business, branding, health, life. No fluff. Real talk about building something that matters while the clock’s ticking. Whether you’re running your first mile or your hundredth company, we’re here to help you go the distance. Because almost there isn’t good enough.
Episodes

Saturday Oct 04, 2025
Saturday Oct 04, 2025
Will your business show-up in AI search? Here's the test...
AI is rewriting the rules of search — and business owners can’t afford to ignore it. Joe had a private meeting with execs from OpenAI (ChatGPT) and cuts through the noise to share how businesses need to adapt. From optimizing websites for AI engines to creating content that actually goes from discoverability to relevancy, we break down the shift from Google to ChatGPT, Claude, and beyond — and why it matters for your business right now.
5 Key Takeaways:
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AI will be the new search engine — queries are increasingly starting in ChatGPT or Claude, not Google, and the difference in user experience should inform your business strategy.
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Your website is (still) your foundation — clear, structured, modern sites rank better with AI-driven engines, so don't get cute with content.
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Platforms matter — Shopify is building AI integrations; outdated systems could leave you invisible. (And this isn't just an e-commerce concern.)
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Content wins — original, relevant writing will still drive organic traffic but will also create engagement WITHIN AI. (Hint: quality over quantity, but quantity too.)
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Pro tip: Publishing directly within AI platforms like Claude is a current hack to boost visibility (and that's the low-friction way toward quantity).
Plus Joe leverages his expertise in SEO and digital marketing to assess the fast-moving impacts of AI search and offer actionable tactics to test go-to-market strategies right now.

Saturday Sep 27, 2025
A Warning for Entrepreneurs: When Leaders Become Managers Business Growth is at Risk
Saturday Sep 27, 2025
Saturday Sep 27, 2025
What makes a great leader different from a great manager? Joe confesses why one-on-ones drain him, what he learned in the Boardroom of a publicly-traded company about persistence, and how changing environments can unlock hidden potential -- especially with support from good managers.
Key Takeaways:
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CEOs and entrepreneurs need to know the difference between leadership and management (and then prioritize their roles accordingly).
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How recurring 1-on-1 meetings can become a waste of time—and the alternative that works better.
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How changing environments helps people see -- and know -- what they couldn’t before.
- Why making others look good isn't just cynical career growth advice.
Plus Joe shares real-life observations from the boardroom that have shaped his leadership style as an entrepreneur: be persistent, give tough feedback well, and trust your direct reports to get sh*t done.

Saturday Sep 20, 2025
Unlock Value & Scale Faster By Betting On People Not Just Plans
Saturday Sep 20, 2025
Saturday Sep 20, 2025
Joe dives into the art (and risk) of hiring ahead of where your business is today. From bringing in talent before the role exists to structuring equity and vesting agreements, we explore how the right people can accelerate growth—or hold you back. Learn how to balance vision with reality when building your team.
5 Key Takeaways:
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Hire forward, not backward: Bringing in talent for where you’re headed—not just what you can afford today—can unlock faster growth.
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Roles can follow people: Sometimes the right person shapes the role, not the other way around.
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Know when to find partners vs. contractors: Equity can fill critical gaps when you can’t pay market salaries.
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Use vesting to de-risk equity grant: Protect both founders and hires by aligning incentives over time.
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Disruption requires buy-in: A great team challenges norms but stays aligned with the CEO’s long-term vision.

Saturday Sep 13, 2025
Saturday Sep 13, 2025
The Leadership Hack to Turn Discomfort Into Collaboration
Conflict is inevitable as teams grow—but how you handle it makes all the difference. Joe describes real-life examples of why ambiguity is the root of many workplace tensions, how to spot it early, and the fastest way to resolve issues before they spiral. From surprise three-way calls that cut through the noise to creating space for empathy, you’ll hear practical strategies for quickly turning conflict into collaboration.
Key Takeaways:
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Ambiguity is an early warning sign: conflict often comes from poor communication and can turn into "us" vs. "them."
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Speed wins: the quicker you address an issue, the less damage it causes.
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Being direct can be uncomfortable: and that tension can drive effective change.
- Encourage open dialogue: empower teams to solve problems without escalation.

Saturday Sep 06, 2025
The 1 Question for Founders That Will Redefine How You Spend Time
Saturday Sep 06, 2025
Saturday Sep 06, 2025
How to unlock enterprise value, delegate effectively & adapt systems to match goals
We dive into the most persistent question every founder faces: "where should you really spend your time?" From making pizzas in the early days to building national marketing campaigns, Joe shares how he decides what drives enterprise value, how he makes delegation an effective priority, and how to balance what fuels you with what fuels the business.
5 Key Takeaways:
- Every “yes” is also a “no”: time is your scarcest resource. When you say yes to one thing you are saying no to something else. Choose wisely.
- Delegate early in the day to unlock team productivity: if you’re the bottleneck, everything slows down.
- Get in the weeds with curiosity: you don’t need to know it all, but you need to bring broad perspective to seemingly small decisions.
- Reevaluate goals often: what mattered last year may not matter today and so your processes may be outdated.
- Processes are hidden resources: multiply time and enterprise value.
Plus Joe makes a confession about being the Chief Optimist.

Saturday Aug 30, 2025
When "Brilliant" Ideas Bomb: Critical Lessons for Escaping Your Own Bias
Saturday Aug 30, 2025
Saturday Aug 30, 2025
What We Learned When No One Wanted What We Loved (and how that saved us money!)
A/B testing online for customer preferences was a tried and true strategy for Joe as he built websites and digital marketing campaigns in the automotive space, but how could he apply those lessons for CPG retail in the "real world?" He shares a wake-up moment as a founder about confidence, bias, and the importance of testing ideas before scaling. From launching a canned water experiment that looked clever on paper—but creeped people out in real life—to uncovering what customers actually want, this conversation is packed with lessons for entrepreneurs who think their “gut” is enough.
5 Key Takeaways:
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Your confidence doesn’t equal customer preference: Watch, listen and learn from your customers especially in early stages of product development.
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How to test in the real world to prevent expensive mistakes: simple DIY experiments can yield valuable insights.
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If you're inside the bottle, you can't read the label: Good branding is important but being overly clever can backfire when customers don’t “get it.”
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Data beats opinions: whether from surveys, ads, or in-person experiments you don't need a lot of data to make better decisions and you've got no excuse for not collecting data.
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Tips to avoid paralysis by analysis: meet your customers where they are, test only what matters, and keep going.

Saturday Aug 23, 2025
How I lost 50 lbs in 6-months and designed a health routine that saved my life
Saturday Aug 23, 2025
Saturday Aug 23, 2025
Tips to Approach Diet & Fitness: Test, Track & Take Action Now
Joe gets candid about his journey from neglecting fitness while grinding to grow his business to losing 45 pounds, running marathons, and sustaining healthier habits to be a better business leader, father, and husband. The connection between entrepreneurship and personal health is often overlooked so we break down the myths of “perfect routines,” why waiting until “next week” never works, and how small changes with realistic expectations can transform both your health and your business. Plus Joe shares his own shortcomings to help others assess what’s right for their own lifestyles.
Key Take-Aways:
- Start Now, Not “Next Week:” Putting off health until “Monday” or “after the holiday” is just a delay tactic. If you don’t tolerate delays in your business, why would you delay making changes to improve your health?
- Better Health = Better Leadership: Prioritizing fitness and diet leads to greater energy, mental clarity, and confidence, directly impacting performance as an entrepreneur.
- Sleep Is the Foundation: Without adequate rest, exercise and nutrition won’t deliver results—protect your sleep first.
- In Your Diet, Track Weeks, Not Days: Weight loss and body transformation are 90% diet; tracking calories and protein intake is a game-changer, but you have to track results over weeks, not days.
Accountability Creates Momentum: Challenges, races, or workout partners provide the structure and motivation to stick with new habits.

Saturday Aug 16, 2025
These Hard-to-Believe Moments Made Me a Better Entrepreneur (AMA)
Saturday Aug 16, 2025
Saturday Aug 16, 2025
Rule of Thirds for Startups: Big Wins, Paper Cuts & When to Call a Spiritual Healer
In an Ask-Me-Anything episode Joe shares intimate stories from behind the scenes of starting and running his businesses including the surreal moment of getting a $200+ Million offer and when the only solution was to call a spiritual healer to cleanse the business.
Key Take-Aways For Entrepreneurs:
- Measuring growth in thirds to find the right balance
- Why you should keep banging on the doors of opportunity
- How to handle wins that validate risk and losses that can't be corrected
- How losing key employees can be a time to reset operational needs
- Having an optimistic attitude to protect against unpredictable setbacks

Saturday Aug 09, 2025
Run Smarter Facebook Ads: How I Hacked the Algo
Saturday Aug 09, 2025
Saturday Aug 09, 2025
Hijacking Super Bowl Commercials. Brand vs. Performance Marketing. Social Proofs Ads vs. Demographic Targeting.
Feeling stuck on how to start marketing on Facebook, Instagram or Google? Joe cuts through the noise to share a simple and proven, early-stage business strategy. Learn how to build buzz, drive sales, and make every dollar work harder—without falling into the common traps that drain budgets. From hijacking big brand moments to letting the algorithm find your perfect customer, this episode gives you the blueprint to build your online business.
Key Takeaways:
- Brand + Performance Marketing: Master the two-part formula for awareness and sales.
- PR is your secret weapon—and your ad content goldmine.
- Ride the wave of competitor campaigns and cultural moments (Go Brewing landing pages vs. Heineken Zero Super Bowl commercials).
- Feed the algorithm with creative variety, not guesses at demographic targeting.
- What metrics to measure so your ads pay for themselves.
Joe shares expert advice based on his experience building and selling two companies that were at the forefront of digital marketing, as well as real-world examples building a non-alcoholic beverage company that sells online.

Saturday Aug 02, 2025
The Set-and-Forget Playbook for 30% More Revenue (Already Hidden in Your Business)
Saturday Aug 02, 2025
Saturday Aug 02, 2025
Build Email Flows that Unlock Value, Drive Sales & Create Relationships
The most undervalued resource of your business is your ability to contact customers directly so why would you spend money to drive people to your website or store if you can't stay in touch with them? In this episode Joe explains why you shouldn't spend money on ads until you build a system to earn customers' contact information and then send emails (or text messages) that will:
- turn visitors into customers
- create long-lasting customer relationships
- uncover customer insight that will help improve your product or service
- reduce your advertising costs
- develop social proof to validate your business
Joe shares a behind-the-curtain look at the automated email flows that he developed for Go Brewing and Easy Man, but these practical tips can apply to any business even ones that are not in e-commerce.
