What if AI isn't the threat - but the greatest ReInvention Accelerator of your lifetime?

In this episode, we sit down with Bill Gurley (legendary Benchmark partner; early investor in Uber, Zillow, Grubhub) to talk about his new book Runnin' Down a Dream and the principles behind building a career you actually want.

Bill breaks down why so many people feel stuck on the "college-to-safe-job conveyor belt," and why mid-career can be the best time to make a change - if you approach it with the right mindset. We dig into the difference between low agency (AI feels terrifying) and high agency (AI becomes jet fuel), and Bill shares a practical framework for exploring your next chapter without blowing up your life overnight.

In this conversation, we cover:

• Why career regret is so common, and how to reverse it
• Bill's "Never Too Late" philosophy for mid-career reinvention
• How to build a "dream job folder" and test your next path before you leap
• The smartest way to use mentors, peers, and aspirational models
• Bill's blunt advice on AI: you can't stop it, so learn to wield it

If you're navigating burnout, uncertainty, or the feeling that your work isn't you anymore, this episode is a permission slip + a playbook. If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next.

www.ReInvention.biz

**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

Leaving corporate can feel like freedom, until you hit the point where building your next chapter can feel incredibly lonely. In this episode, Chris and Todd tackle a ReInvention challenge most people don't see coming: Isolation - and how being isolated quietly drains your energy, creativity, and momentum when you're launching something new.

In this episode you'll get practical, real-world strategies to stay connected while working independently that include a few JEDI techniques to spurn amazing creativity:

• Integrating 2–3 non-work anchors (sports, classes, hobbies) into your weekly rhythm
• Using walks and neighborhood connection as a daily reset
• Changing where you work (cafes, coworking, "micro-commutes")
• Creating intentional "CEO-level" work trips (conferences, meetups, learning rooms) to replace the structure corporate used to provide.

We also talk about how to use technology as a tool for real rapport, not transactional Zoom fatigue - and why being proactive about connection isn't a luxury but part of your ReInvention plan.

If you're reinventing your career, starting a business, consulting, or building a portfolio career, this episode will help you stay human, stay motivated, and build community on purpose.

If this conversation resonates with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next.

www.ReInvention.biz

**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

If you're the primary breadwinner or you carry the "provider" identity, Career ReInvention can feel impossible. The fear is real: If I change jobs, the whole system collapses. Mortgage. Bills. Kids. Expectations. Your nervous system starts treating reinvention like a threat.

In this episode, Chris and Todd unpack the Provider Trap - the hidden identity that keeps high-achievers locked into misaligned work long after it stops working. They talk about why "providing" is more than a paycheck (presence, energy, relationships, legacy), how fear and scarcity get passed down through generations, and why staying in the wrong career can quietly cost you the very family life you're trying to protect.

They also get a bit personal with their own stories. Chris reflects on losing his dad when he was 25 and the conversations they had towards the end. Todd shares some personal challenges he and his wife are currently dealing with when it comes to the question: 'What is a breadwinner - and what are we really providing'.

At the end you'll understand why courage is the most important muscle that makes ReInvention possible - even when you feel like you have no room to fail.

If you've ever thought, "I can't change - everyone depends on me," this episode is for you.

If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next.

www.ReInvention.biz

**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

ReInvention can be stressful. Uncertainty ramps up anxiety, drains your energy, and can pull you into numbing habits that keep you playing small.

In this episode, Todd and Chris break down a simple way to protect your momentum: build a daily "scaffold" that boosts vitality, focus, and optimism while you're reinventing your career.

You'll learn:

• Why most reinventors struggle when they leave the structure of corporate life
• How to replace that structure with habits that are healthier and 'more human'
• A series of basic, high-impact practices for your morning and evening routines
• A proven way to wind down at night and improve sleep (reducing mental noise)
• How to stay motivated and positive as you're in transition

Chris also shares some useful strategies like removing your phone from the bedroom and switching from doom-scrolling to reading, so your brain can actually recover.

If you're in a career transition, building something entrepreneurial, or just trying to avoid burnout while you figure out "what's next," this episode gives you a grounded, repeatable system to stay strong - physically, mentally, and emotionally - so you can make better decisions and move forward with confidence!

If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next.

www.ReInvention.biz

**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

If you're building a consulting practice, doing some fractional work, or starting any kind of entrepreneurial / "hang-my-shingle" venture, here's the truth: your results won't matter if you can't sell.

In this episode, Todd and Chris break down sales in a way that's clean, human, and repeatable - especially if you've spent years in corporate and the word "selling" makes you tense up.

You'll learn why the best sales conversations aren't about pitching harder, they're about listening deeper.

• The 4 key Pillars within any business - and a way to identity your strong suits and weak areas
• The shift that changes everything: you're not selling a product - you're selling a future outcome
• Why "deep curiosity" beats persuasion (and how it makes closing feel natural)
• The moment most people avoid: asking directly for the sale (and how to do it without getting weird)
• The power of silence after the ask - and how to handle objections without spiraling
• A key skill most people skip: expertise in the manner by which you actually sell (online vs. phone vs. face-to-face, for example)

If you've ever thought, "I'm great at what I do… I just don't know how to sell it," this is your episode.

If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next.

www.ReInvention.biz

**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

If you're in the middle of a career transition, you've probably felt this tug-of-war:

Part of you knows you need space… time to decompress, process what happened, and heal from the emotional toll of your old work life.

Another part of you feels intense pressure to move fast… to make money again, prove this wasn't a mistake, and "figure it out" as quickly as possible.

In this episode, Todd and Chris unpack the real (and rarely discussed) dilemma: how to balance healing with forward momentum so you don't get stuck in reflection…and you also don't rush into the same patterns that created the burnout in the first place.

Inside the conversation:

• Why "push through" works, until it doesn't
• The hidden cost of skipping the processing/healing phase
• How financial runway (and real-life situations) change the pace of ReInvention
• Why taking time to reflect often accelerates new successes instead of delaying them
• A practical way to build self-reflection into daily life while still moving forward
• What it looks like when your work finally feels integrated with who you are

This is an honest, human episode for anyone who's trying to build what's next without ignoring what the old chapter did to them.

If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next.

www.ReInvention.biz

**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

Fear. Doubt. Anxiety. The mental spiral that makes everything feel heavier than it actually is.

In this episode, Todd and Chris go straight into the "real stuff" that shows up when you're in transition or uncertainty - especially when you're trying to make a big change and your nervous system starts writing worst-case stories.

We break down a simple truth: your emotions can feel urgent… without being supported by objective reality. And we give you practical tools to stop the spiral, separate facts from fear, and turn "negative" emotions into forward motion.

In this conversation, you'll learn:

• Why your nervous system can react like the world is ending - even when the numbers say you're okay
• How to tell the difference between real fear and "rollercoaster fear"
• A simple method to sort what's valid vs. imagined
• The "control the controllables" mindset shift (and why it saves massive energy)
• Why numbing out (Netflix, distractions, checking out) keeps you stuck - and what to do instead
• The Allow & Reflect practice Todd uses to process fear and generate solutions

If you've been feeling stuck, frozen, or caught in old conditioning… this episode will give you a framework to work with fear - without letting it drive the car.

If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next.

www.ReInvention.biz

**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.

Ever feel that little spike of anxiety when someone asks: "So… what's going on with work?"

If your career is shifting, evolving, or in a "between chapters" season, that question can make even the most capable people freeze - not because they're failing… but because they don't yet have the language for what's emerging.

The FIX here is so simple, and instantly adds so much confidence back into whatever you're doing, but most people simply don't know the power of crafting communication scripts….

In this episode, Todd and Chris break down a simple 5-step communication framework that helps you speak about where you are right now with clarity, confidence, and authenticity - without oversharing, sounding uncertain, or falling into the "woe is me" trap.

You'll learn how to:

• Acknowledge your past without getting stuck in it
• Name the transition (without making it awkward)
• Share what's real in a way that builds connection (not discomfort)
• Shift the conversation toward possibility and momentum
• Make a confident "ask" that can create real opportunities (introductions, ideas, next steps)

This is the kind of small skill that quietly changes everything: your confidence rises, your relationships deepen, and your conversations start opening doors again. Listen to this whole episode as we provide detailed scripts throughout!

If this conversation resonated with you, visit ReInvention.biz to explore our guided workbook and join a community of people just like you - people designing what's next.

www.ReInvention.biz

**Subscribe to the ReInvention Podcast to stay plugged into fresh ideas, frameworks, and real-world tools for navigating the future of your work and life.