Have you ever looked around at your tech company and realized you’re one of the oldest people in the room…and you may not even be 40 yet? It gets late early is a podcast and community focused on the experience of aging as a tech employee. We’ll uncover the root of Silicon Valley’s obsession with youth, and parse fact from fiction. We’ll explore individual experiences across tech companies of various sizes, learn from experts, and share practical advice on how tech workers can build long and fulfilling careers in tech - for as long as they want - or need - to be employed. Together we’ll discover how we can all bring about a better future - for tech companies and employees alike.
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How to Build Something New After 40 (Even When It Feels "Too Late")
Épisode 67
mardi 16 décembre 2025 • Durée 52:36
"It's too late for me."
I had this worry, but I finally hit publish on my first podcast episode at 40.
I thought I'd missed the boat. Everyone else had already started, and I wondered if I was too old to become a creator in an industry that thinks you expire at 35. I was terrified to try something new in public.
But here's what I've learned: that "too late" feeling? It's just plain old straight-up fear wearing a really convincing disguise.
I feel so strongly about debunking this myth that today, in this special episode, I get the chance to flip the mic and be interviewed by Rhona Barnett-Pierce on her podcast, Workfluencer. We're getting into all the messy, uncomfortable stuff about starting something new when you feel like you've missed your window.
We talk about:
→ The year I spent overthinking instead of doing (and why that was such a waste)
→ How to actually start when you don't feel ready (because you never will)
→ Why your age might actually be the thing that makes you better at this
→ What to do when people think you're cringe (spoiler: you gotta lean in)
→ Where to find support when your friends and family don't get it
→ The real timeline from "I'm terrified" to "okay, I'm doing this"
This conversation is for you if:
→ You've been thinking about starting something but keep finding reasons to wait
→ You're staring down a layoff or career pivot and don't know what's next
→ You want to build something of your own but feel like you've missed your chance
→ You're tired of the voice in your head saying "not ready yet"
→ You need someone to tell you it's okay to be scared and do it anyway
Look, I'm not going to tell you it's easy. Starting something new at 40—especially something visible like starting a new business or jumping into content creation—is uncomfortable as hell. But the alternative is spending the rest of your life wondering "what if?" And I really, really don’t want that for you.
At the end of the day, “everyone's cringe until they make it. Then people pretend they supported you all along." (Thanks to my 28-year-old social media consultant for that gem.)
I hope this conversation gives you permission to just start. Scared, unprepared, "too old," whatever. Just start. Let’s make 2026 the year you go for it, whatever your “it” might be. The world needs you!
Speaking of 2026, we’ll be taking a holiday break til then. Happy Holidays to you and yours!
Tech Layoffs, Ageism & AI: Is a Tech Career Still Worth It?
Épisode 66
mercredi 26 novembre 2025 • Durée 54:39
Tech isn’t just in a downturn. It’s in the midst of a full-blown identity crisis. As layoffs, ageism, and AI reshape the workforce overnight, Brian Pulliam joins me to break down what’s actually happening behind the scenes… and what mid-career professionals must do to stay competitive.
Brian, a former tech leader who spent 23 years at companies like Microsoft, Zillow, and Coinbase, joins me to talk about a controversial topic. With tech experiencing year-after-year meltdowns, Brian offers a brutally honest look at whether anyone should still pursue a tech career in 2025–2026.
He breaks down why the job market feels broken, why entry-level roles are disappearing, and how AI is replacing the very apprentice-level opportunities that used to grow workers into senior talent. He also explains why employers are pulling back on long-term investment, what the real supply-and-demand curve looks like, and why ageism is hitting harder and earlier than ever.
We discuss strategies for standing out in an oversaturated market, how to approach salary discussions, and the mindset shifts every experienced employee needs to remain competitive in a chaotic and unpredictable hiring landscape.
If you're feeling overwhelmed by tech layoffs, frustrated by age bias, or unsure how to pivot in today’s wild job market, this episode gives you clarity, direction, and a whole lot of real talk.
Do you want Brian to help you navigate the tech job market or level up your career? Mention you heard him on It Gets Late Early and get 20% off any coaching package when you book through his site or connect via LinkedIn.
I Paid $48K for Health Insurance and Still Owed $10K—So I Built a Solution
Épisode 65
jeudi 13 novembre 2025 • Durée 01:14:45
With mass layoffs hitting tech, media, and corporate America, more professionals over 40 are being forced into freelance work, consulting, and solopreneur life—whether they planned for it or not. And here's a big problem with that: the moment you leave corporate, you lose access to affordable health insurance. Suddenly, you're staring down $4,000/month premiums, sky-high deductibles, and hospital bills that make you wonder what you're even paying for.
In today's episode, I sit down with Crystal Jackson—also known as The Real Mrs. Poindexter—a former Intel engineer turned viral content creator with millions of followers. After 13 years in corporate, Crystal left to raise her kids, went back to work for the benefits, left again, and eventually found herself paying $48,000 a year for health insurance that barely covered anything. When she got sick and ended up with another $10,000 in medical bills, she'd had enough.
So she did what any fed-up engineer would do: she co-founded EssentL Creator with her husband Chris to solve the problem no one else would touch—affordable, corporate-level health insurance for freelancers, gig workers, and solopreneurs.
In this episode, we talk about:
Why Crystal was paying $48K/year for health insurance and still owed $10K in hospital bills
How the "future of work" is creating a wave of involuntary entrepreneurs (and what that means for you)
What a PEO (Professional Employer Organization) actually is—and how it gives solopreneurs access to corporate-level benefits
Why leaving corporate might be the scariest—and best—thing that ever happens to you
How to protect yourself legally and financially when you go out on your own (LLCs, IP protection, contract red-lining)
The mental health crisis among content creators—and why EssentL offers enhanced mental health and addiction coverage
If you've been laid off, are thinking about going solo, or are tired of paying insane premiums for garbage coverage, this episode is for you. Find a gift of the admin fee for It Gets Late Early listeners at .
AI Is Teaching Us to Hate Our Own Faces - Former Google Employee Turned Artist Exposes the Truth
Épisode 64
mardi 28 octobre 2025 • Durée 54:16
Ever wondered why AI thinks you need to look younger? In this episode, Gretchen Andrew, a former Google employee turned artist, exposes the disturbing truth about how beauty filters are literally reshaping our faces—and our self-worth.
We kick things off with Gretchen's bold pivot from Silicon Valley to the art world, where she's using robots, oil paint, and yes, glitter to reveal what beauty filters actually do to us. Her groundbreaking "FaceTune Portraits" physically apply AI beauty standards to paintings, creating violent scars and marks that show the hidden damage these "harmless" filters inflict on our identities.
Gretchen breaks down the dirty secret of AI training data—how algorithms learn beauty from the most biased corners of the internet and create a feedback loop that makes everyone chase the same impossible standard. Even Miss Universe contestants aren't "good enough" for AI filters, and men in their 50s are rescheduling meetings just to use Zoom's "touch up my appearance" feature!
From Hollywood actresses getting the same face-altering procedures to look good on small screens, to the shocking reality that social media may have incentivized us to provide facial recognition data for free, this conversation will change how you see every filter, every app, and every "enhanced" photo you encounter.
Whether you're tired of the algorithmic beauty trap or just want to understand why everyone's starting to look the same, this episode is essential listening. Gretchen's insights will make you question everything about digital beauty—and maybe even inspire you to embrace what makes you uniquely human.
“The question is: Do you want to look old and like yourself, or do you want to look like everybody else and look younger?”
~ Gretchen Andrew
The Hoodie Myth Is Dead: Why the Best Tech Founders Are Over 40
Épisode 63
mardi 14 octobre 2025 • Durée 14:16
What if everything you thought you knew about startup success was wrong? In today’s episode of It Gets Late Early, I’m breaking down the myth that young, hoodie-wearing entrepreneurs are the key to successful startups. Spoiler: the data proves otherwise.
According to MIT research, the average age of a high-growth startup founder is 42 — not 21. The top 1% of founders are even older, typically around 45 years old. Yet, venture capitalists continue to invest in young, inexperienced founders, ignoring the seasoned leaders with decades of experience.
I also tackle the growing age discrimination in tech, where older workers are pushed out despite having the experience and connections that drive success. Companies that embrace diverse ages and experiences in their teams are the ones that succeed.
Let’s flip the script on startup success. It's time to stop assuming that youth equals innovation. It’s never too late to go after your dreams, and age is an asset, not a liability.
“So just why is it that older workers tend to be more successful? Two words: life experience.”
~ Maureen Wiley Clough
In This Episode:
-Research from MIT: the truth about successful startup founders
-The age bias in venture capital and tech hiring
-Why older founders have an advantage over younger ones
-The challenge to venture capitalists: stop funding failure
-Encouraging older tech workers: your experience matters
And much more!
The $259B Problem Hiding in Your Meetings — and How to Solve It
Épisode 62
mardi 30 septembre 2025 • Durée 42:21
Meetings. Ugh. We’ve all been there, right? And the price tag is bigger than most people realize. We estimate that the cost to organizations of these unproductive meetings is approximately $259 billion in the United States and $64 billion in the United Kingdom for professional staff alone (LSE report). That’s a jaw-dropping drain on productivity—yet it’s largely preventable.
In today’s episode of It Gets Late Early, I’m joined by Dr. Daniel Jolles, a behavioral scientist and psychologist at the London School of Economics, who’s back for his second appearance. Dr. Jolles and I go deep into the world of generational diversity in meetings, exploring how getting it right can significantly boost productivity and reduce wasted hours.
We’re also tackling the elephant in the room: AI in the workplace. With organizations now mandating the use of AI, how can we, across all generations, navigate this technology without falling victim to bias or further exclusion?
We cover the shocking stats about how unproductive meetings cost businesses billions each year and how companies can make sure that no one, especially older workers, gets left behind in the AI race.
Trust me, this episode is a wake-up call. If you’re looking to fix your meetings, ensure inclusivity, and stay ahead in the AI-driven future, you don’t want to miss it.
“We find that there's a huge lack of generational diversity happening in our meetings. Our research suggests that that's hurting productivity because there are diversity benefits to be gained by having voices from the younger and older employees present in meetings, especially when it comes to big-decision meetings.”
20% Fake Jobs. 31% Never Hear Back. What Are Companies Doing?
Épisode 61
mardi 16 septembre 2025 • Durée 40:29
Ever applied, interviewed, and…silence? You’re not alone. In this episode, we crack open the hiring black box: the rise of ghost jobs (roles that never close or never existed in the first place), the avalanche of AI-boosted applications, and why 31% of rejected candidates never even get an email.
My guest Ariana Moon, VP of Talent Planning & Acquisition at Greenhouse, a software platform managing the hiring process, explains how their Greenhouse Verified badges reward employers who actually walk the talk—communication, fairness, respect, and preparation—so candidates can spot companies that treat people like people.
We also get real about what great hiring actually looks like: structured scorecards, clear rubrics, and leaders who blend experience with fresh perspectives. Ariana shares lessons from a very millennial workforce moment (when ~10% of the company went on parental leave at once!) and how Greenhouse supports parents with thoughtful leave, re-entry, and caregiver communities—without letting careers evaporate.
Whether you’re job hunting or leading a team, this episode is a playbook for a fair, respectful, and effective process—because employer brand is a long game, and candidates remember how you made them feel.
Update:Since this recording, Ariana has given birth to a healthy baby boy! Both mom and baby are doing great.
“Greenhouse Verified is a way that we can signal to the talent market that we are a company that prioritizes things like good communication, being prepared in how we run our interview processes, being fair in how we think about our interview processes, and being respectful when we're interacting with candidates. ”
~ Ariana S. Moon
70% of the Money. Zero Attention — or Employees. What Are Brands Thinking?
Épisode 60
mardi 2 septembre 2025 • Durée 48:44
Marketers love chasing Gen Z. But here’s the trillions-of-dollars blind spot:
Gen X and Boomers control nearly 70% of U.S. disposable income and outspend younger generations in nearly every major category — alcohol, beauty, travel, finance, and more.
So why are brands still ignoring them?
In this episode, I sit down with Brent Rivard, founder and CEO of Geezer Creative, an agency built on a radical idea: the “forgotten generation” isn’t just relevant — they’re the growth engine brands are missing.
We unpack how the ad industry’s obsession with youth culture has aged itself out of opportunity, what’s at stake for marketers, and how Gen X and Boomers are reshaping the creative economy.
You’ll also hear shocking stats about how the industry treats its veterans, the challenges older professionals face in a rapidly evolving gig economy, and why AI is becoming a make-or-break skill for creative professionals of every generation.
Because if brands keep underestimating us, that’s on them. But if we underestimate ourselves? That’s on us.
The creative economy is shifting fast — from AI to the rise of the gig economy — and this conversation will give you a fresh (and dare I say slightly rebellious?) perspective on where your experience fits next.
“The last thing the world needed was another ad agency, so we opened one. But we didn't just open one–we opened one that has a point of view.”
~ Brent Rivard
The 10% Rule: Why a Little More Vulnerability Can Change Everything With Will Greenblatt
Épisode 59
mardi 19 août 2025 • Durée 50:34
Why is it terrifying to present to just four people? According to Will Greenblatt, it's because our brains still think the tribe might "club us over the head" if they don't like what we say.
Will's journey from Canadian child actor (yes, a self-proclaimed "nepo baby") to sought-after corporate speaking coach is anything but typical. After working with Anne Bancroft as a kid and nearly getting swept up in the Hollywood machine, a family tragedy and toxic theater school experience led him to completely reinvent himself.
But here's what makes this episode essential listening: Will discovered that the same skills that make great actors also create breakthrough leaders. The difference? It's not about performing—it's about finding emotional truth and connecting authentically with your audience.
The game-changing insight: When Will's clients embrace just 10% more vulnerability in meetings, they see measurable career improvements—better performance reviews, more influence, and stronger professional relationships. Because while everyone else is playing it safe, that small dose of authenticity makes you unforgettable.
We dive deep into why mentorship is broken in today's workplace, how to spot genuine people in interviews, and Will's three-act framework for storytelling that builds instant trust. Plus, he shares the uncomfortable truth about why taking career risks, like leaving acting or corporate, might be the safest move you can make.
“You give somebody the opportunity to destroy you, and you hope that they won't, and they might. But you can't love without that risk. And it's the same kind of thing when you tell your boss what you really think.”
~ Will Greenblatt
In This Episode:
Fired and Diagnosed With Cancer: How Daniel Incandela Rebuilt His Life
Épisode 58
mardi 5 août 2025 • Durée 39:34
Losing a job is never easy, but what if it led to a more fulfilling path? Daniel Incandela, former CMO, opens up about the painful yet transformative experience of being fired in his 50s. In this episode, he shares the emotional toll it took, how he navigated the challenges, and the powerful lessons he learned along the way.
Today, I sit down with my good friend, Daniel Incandela, who, like many of us, faced the harsh reality of burnout and being let go. His story is one of resilience and transformation. Despite the painful blow of being fired, Daniel reflects on how the experience helped him realign his priorities, focusing on family, health, and ultimately finding his path forward through consulting and creative work.
We discuss the importance of reflection and accountability, even in the most challenging moments. Daniel’s journey sheds light on how career paths don’t always go as planned, and how the pressure to “do it all” can weigh heavily on us. From navigating ageism in a competitive job market to embracing AI as a necessary tool for today’s workforce, Daniel discusses how he’s finding purpose in his new role and working towards a future that aligns more with his values.
If you’ve ever felt like your career took an unexpected turn, this episode is for you. Daniel’s story is a powerful reminder that we can find clarity even in moments of doubt.
“I've been on this journey that I think I really needed in life, and it has helped me awaken from things I did not see.”
~ Daniel Incandela
In This Episode:
-Daniel’s transition from CMO to consultant
-Embracing change and realizing what really matters
-Leadership in the time of AI
-The reality of getting fired in your 50s
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