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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.
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

4 days ago
4 days ago
This is bigger than the Internet. It's a new way of being in the world. And its transformation of "work" is a force multiplier.
(Part 3 in a mini-series on how to use AI now.)
Most people think AI is a tool you learn, like Excel. It's not. It's something you have to learn to think with — and that changes everything. Joe and Dakota discuss why the people who get that now will be years ahead of everyone else, and why the ones who don't are already behind.
What you'll learn:
- Why AI isn't a skill to acquire but a relationship to develop — and why that distinction matters more than most people realize
- How curiosity has become the single most valuable career (and life) asset you can have right now
- The question AI is forcing all of us to ask: if you didn't need the money, what would you actually do with your time?
- Why the barrier to building something — an app, a business, a life — is smaller than it has ever been
- How Joe is using AI inside Go Brewing right now, from sales strategy to accounting to employee training and engagement
For: Anyone who wants to stop reacting to the future and start building it.
Topics: artificial intelligence, future of work, entrepreneurship, personal development, career strategy, AI tools, mindset, productivity

Saturday Mar 21, 2026
The biggest competitive advantage right now isn't money or talent.
Saturday Mar 21, 2026
Saturday Mar 21, 2026
This is what democratized tech solutions look like, for business and life.
(Part 2 in a mini-series on how to use AI right now.)
From a custom app that rewards his son's treadmill miles with screen time to a personal news feed curated around his exact interests, to developing a bespoke headless commerce app for his business, Joe makes the case that anyone, not just entrepreneurs, can now design the technology experiences they've always wanted but never had.
Discussion Highlights:
- How AI makes asking the right questions such a powerful habit
- What headless commerce is and why it matters for businesses of any size
- How APIs connect platforms like Shopify, Klaviyo, and Peloton into seamless custom experiences
- How to stop paying for software that almost fits and instead build tools exactly fit your needs
For: Business owners, entrepreneurs, parents, and anyone who has ever used a product and thought — I'd have built this differently.
Topics: headless commerce, API integration, e-commerce personalization, AI tools, democratized technology, custom apps, small business software

Saturday Mar 14, 2026
Saturday Mar 14, 2026
Googling Gives You Answers. AI Builds Tools to Solve Your Problems. Just Ask It.
(Part 1 in a mini-series on tips for using AI)
Most business leaders are using AI to draft emails and summarize documents. Joe is using it to build custom operating systems, automated and integrated CRM platforms, and lead-scoring tools — without writing a single line of code. The biggest unlock isn't knowing how to code. It's knowing how to describe your problem.
In this episode, Joe walks through real examples from his own businesses — including how he automated a multi-step wholesale retailer approval process that used to take an hour — and shares how he helped a nonprofit CEO realize AI could transform their weekend voicemail backlog into an automated, real-time response system.
Key Takeaways:
- The reason most people aren't unlocking AI's real power isn't a tech problem — it's an imagination problem.
- Describing your problem to AI and asking it to recommend a solution will get you further than knowing the answer yourself.
- Vague prompts get vague results — the more business context you give AI, the more useful and specific its output becomes.
- AI doesn't just tell you what to do, it can actually build the tool that does it — CRMs, lead scorers, anomaly detectors, and more.
- A process that once took an hour across three systems can be fully automated in a single conversation.
For: Business owners, entrepreneurs, and operators across any industry who know AI can do more for their business but don't know where to start.
Topics: AI for business, business automation, no-code tools, AI prompting, CRM, lead scoring, ChatGPT for business, AI productivity, nonprofit technology, operational efficiency

Saturday Mar 07, 2026
If I'd Known Where He'd Been, I Couldn't Have Helped Him Get Where He Wanted to Go
Saturday Mar 07, 2026
Saturday Mar 07, 2026
Why Big Goals Work and How Lived Experience Can't Be Measured
The goal was 5:35. The qualifying time for a double amputee to get into the Boston Marathon. It was an outrageous target and Joe had no idea. In this episode, recorded on the road while traveling to an Innovation Summit, Joe shares the Cedric King story that changed how he thinks about goal-setting, performance, and the surprising relationship between the two. What looks like a running story is really a lesson about what happens when you strip away past performance data and commit fully to what's possible.
Key Takeaways:
- Why setting a goal with no baseline can unlock performance that history would have made impossible
- How the experience of committing to a mission — without knowing the odds — is sometimes the only thing that produces the result you want
- The difference between chasing a measurable outcome and being present to what's actually in front of you
- Why your previous PRs, past failures, and historical data can be the very thing capping your next breakthrough
- What Cedric King's Boston qualifier teaches entrepreneurs and leaders about the danger of "realistic" goals
- How lived experience creates a kind of value that metrics will never capture — and why that matters for how you lead, build, and grow
For: Entrepreneurs, business leaders, coaches, athletes, and anyone who has ever let past results talk them out of a goal worth chasing.
Topics: Goal setting, outrageous goals, performance vs. experience, Boston Marathon, Cedric King, guide running, double amputee athlete, business mindset, leadership, ignoring past performance, what's possible

Saturday Feb 28, 2026
Why are you letting “them” steal your joy?
Saturday Feb 28, 2026
Saturday Feb 28, 2026
How to align information with action, not distraction.
Comparison is the thief of joy — and it might be the thing quietly killing your momentum. Joe breaks down why watching competitors, obsessively consuming industry content, and chasing every "squirrel" in your feed can keep you from reaching your own destination. To get where you’re going, you have to know why and how you want to get there.
Key Takeaways:
- Why having a vision (not a perfect plan) is the non-negotiable first step in business and health
- How time-bound goals — races, speaking engagements, launch dates — create the pressure that produces real action
- The social media algorithm trap: why consuming content in your own category can deflate you and pull you off course, and a simple but powerful hack to escape the trap
- Why looking outside your industry for inspiration beats studying your competitors
- The difference between distraction and inspiration: how to audit your emotional response to what you consume
For: Entrepreneurs, business owners, brand builders, athletes, and anyone prone to measuring their progress against others instead of their own goals.
Topics: Comparison trap, staying focused, goal setting, time-bound goals, social media distraction, entrepreneur mindset, business strategy, building a brand, joy and motivation, competition vs. vision

Saturday Feb 21, 2026
How to Reinvent Yourself When Your Own Success Is Holding You Back
Saturday Feb 21, 2026
Saturday Feb 21, 2026
What happens when the life or business you've built becomes the very thing preventing you from growing? In this episode, Joe digs into the hard truth that the things (the co-workers, the business structure, the story about who you are and what you do) that got you to where you are today, may not be what gets you to where you ultimately want to go. From the factory floor to entrepreneurship, from personal bouts of injury and depression, Joe reflects on what he’s learned about radical transformation, and the courage it takes to “burn it down” and build something better, including a story about his friend Ben Mollin who inspired the creation of one of Go Brewing’s first beers.
Whether you're an entrepreneur navigating a critical growth stage, a professional feeling stuck in a career that no longer fits, or someone searching for a personal reset, this conversation will challenge the way you think about success, happiness, and starting over.
What you'll learn in this episode:
- Why the team and structure that helped you grow your business may be the very thing holding it back, and how to navigate that transition
- How changing your environment, whether physically or mentally, is often the first and most powerful step toward personal reinvention
- The story of Ben Mollin, a reality TV personality turned ultra-marathoner, and what his radical life reset can teach you about happiness and letting go of success that no longer serves you
- Why hitting rock bottom (economic insecurity, injury, depression) can become the unexpected foundation for your greatest reinvention
- How to recognize when you're being held back by complacency and what it looks like to truly start over
Topics Discussed: Business scaling and team building, fundraising challenges, personal reinvention, changing your environment, overcoming adversity, entrepreneurship, mental health and happiness, minimalism, ultra-running and fitness as transformation, craft beer and brand evolution.
See also Joe’s interview with Ben Mollin:
https://open.spotify.com/episode/3CkJJtggnWzg5jH7Dbnwrx?si=75cbc65d480a4761
An event with Ben Mollin at Go Brewing on March 7 & 8:

Saturday Feb 14, 2026
Why I Became Someone Else to Overcome My Biggest Fear
Saturday Feb 14, 2026
Saturday Feb 14, 2026
The Alter-Ego Trick To Beat Performance Anxiety
Anxiety can be debilitating whether it manifests as a stutter, a bad attitude or feeling stuck. In this episode, Joe shares how he went from a kid with a stutter to a keynote speaker using a powerful mental technique: creating an alter ego. Learn the persona method Joe used to overcome his anxiety, how he taught his daughter to use it for sports performance, and why preparation and repetition are the real keys to building confidence. This episode delivers actionable techniques for turning fear into your greatest advantage.
Key Takeaways:
- How to create an alter ego or persona to shield yourself from criticism and self-doubt
- Why modeling charismatic leaders (like Alan Mulally) can transform your confidence
- The power of gradual exposure: speaking to 5 people before scaling to 500
- How preparation and "doing the work" eliminates anxiety better than any other method
- Teaching the alter ego technique to others (real example with Joe's daughter "Brooklyn")
- Why adversity and struggle in childhood can become your greatest competitive advantage
- The importance of iteration and postmortem analysis in any creative or business endeavor
Key Topics: Public speaking anxiety, overcoming stuttering, alter ego technique, performance anxiety, building confidence, imposter syndrome, parenting advice for athletes, deliberate practice, entrepreneurship mindset, turning adversity into strength

Tuesday Feb 10, 2026
Naming Your New Business is Fun. And VERY Risky.
Tuesday Feb 10, 2026
Tuesday Feb 10, 2026
How to get the trademark you want and need.
Ready to launch and name your new business? Don't file anything until you listen to this. Veteran entrepreneur Joe Chura shares the complete process for choosing a business name that won't get you sued—from Google searches and domain availability to USPTO trademark filing and protecting your brand equity.
Key Takeaways:
- Why Google and GoDaddy aren't enough—the free USPTO search that could save your business
- How to find available business names using NameBoy and trademark class searches
- The phonetic trademark rule that almost cost Go Brewing everything
- When to hire a trademark attorney (and when you might not need to)
- Domain names, social handles, and the "confusion test" explained
- Real story: navigating trademark challenges and calculated risk-taking
Whether you're launching a startup, side hustle, or scaling a brand, learn the step-by-step checklist for securing your business name legally—before you invest in logos, websites, and packaging.
Topics: how to trademark a business name, naming your business, USPTO trademark search, business name availability, domain name strategy, trademark attorney, startup legal tips

Saturday Jan 24, 2026
How to Get Investors to Say Yes to Your Business (Even as a First-Time Founder)
Saturday Jan 24, 2026
Saturday Jan 24, 2026
And why taking a lesser valuation might actually accelerate your growth.
Veteran entrepreneur and investor, Joe Chura, breaks down the critical questions every entrepreneur needs to answer before raising capital—and explains why even successful founders get more "nos" than you'd expect.
What you'll learn:
- Convertible notes vs SAFEs: Which is better for founders?
- Angel investors vs venture capital: How to choose the right fit
- Why investors bet on founders, not just ideas
- The "data story" framework for first-time founders with no track record
- When to actually take investment (and when to avoid it)
Real talk on valuation, dilution, time horizons, and why proving yourself matters more than your pitch deck. Whether you're bootstrapping or ready to raise, this episode reveals what investors are really thinking when they evaluate your business.
For: Startup founders, entrepreneurs seeking funding, business owners considering investment, first-time founders
Topics: Raising capital, angel investors, venture capital, convertible notes, SAFEs, startup funding, founder equity, business valuation, investor pitch

Saturday Jan 17, 2026
Is AI Gaslighting Me or Is Its Over-Confidence a Risk to My Business?
Saturday Jan 17, 2026
Saturday Jan 17, 2026
Can ChatGPT count the Rs in "strawberry"? Joe Chura tests ChatGPT, Google Gemini, and Claude AI with one simple question—and the results expose a dangerous pattern in how AI tools handle mistakes and how business leaders need to validate authority while integrating new technologies into their operations for essential gains in productivity.
If AI can confidently contradict even the Dictionary, how do we make decisions when the tools we trust are simultaneously brilliant and persuasive? The strawberry test raises an uncomfortable question: If AI confidently references sources while giving wrong information, how do you know when to trust it with financial models, spreadsheet calculations, or business decisions?
