TruthWorks

Three friends. One closet. A company now valued at $10 billion, serving over 400,000 small businesses.

Josh Reeves is the co-founder and CEO of Gusto, the payroll, benefits, and HR platform now valued at roughly $10 billion. But he didn't grow up dreaming of building HR software — nobody does. The son of two teachers who were the first in their families to go to college, Josh studied electrical engineering at Stanford during the dot-com collapse, when the conventional wisdom was that the internet was finished. He ignored it. After a stint as a product manager at Zazzle and a first startup he now describes as "stealth mode" — his polite way of saying he had no idea what he was doing — Josh walked away with the most important lesson of his career: never start a company just because your friends are.

In 2011, he and two co-founders started Gusto to fix something genuinely broken. Payroll, benefits, and the systems that quietly reduce people to ID numbers and acronyms — especially in small businesses, where two-thirds of U.S. employers have fewer than five people and every hire is a real human being, not a line item. They set one rule: they wouldn't pay themselves until they could do it through their own product. They launched in December 2012 with 100 small businesses. One co-founder spent four months sleeping on an air mattress in a roommate's closet — it had a skylight, for the record, and the roommate's clothes were still hanging inside.

Fourteen years later, Gusto has grown from three people in a Palo Alto house to over 3,000 employees ("Gusties") across Denver, San Francisco, New York, and Scottsdale — with no headquarters, by design. In this episode, Josh sits down with Jessica to unpack how he protected culture at scale, why he deliberately left revenue on the table to launch in all 50 states the right way, and the framework he uses to resist Silicon Valley's growth-at-all-costs gospel.

You'll learn:
- Why second-time founders have an edge — and why Josh had role, responsibility, and ownership conversations on day one
- The weekly feedback walks the three founders started when they were just three people, and still do 14 years in: three things working, three things to improve
- Why most systems treat people like transactions — and what changes when you build for the human moments instead
- The values-and-motivation interview Gusto uses to hire for what makes someone tick, not just what's on their résumé
- Why interviewing is a skill every leader should practice obsessively — and how the best interviewers dig past the first and second answer to what's really underneath
- How to scale culture without freezing it: "we're not a museum" — what should persist, and what should always be allowed to change
- The "no headquarters" home-base model, and why Josh personally interviewed Denver's first 10-15 hires to make it as important as San Francisco
- Why "doing things that don't scale" early can build the momentum that scales later
- Why he deliberately left revenue on the table to cover all 50 states comprehensively, instead of launching half-built
- The three checks-and-balances Josh runs against growth: product quality and compliance accuracy, unit economics, and team retention
- Why there are over 10,000 payroll rules in the U.S. — and why the business owner should never have to become the expert
- How AI is a tailwind, not a threat — making Gusto more of a teammate and partner to the small business owner
- Why work should be more than a paycheck: purpose, community, and impact, when the alignment is there
- The thought experiment every founder should run before committing: the 10,000th time you describe your idea, will you still be excited?

Whether you're starting a company, scaling one, or just trying to do work that means something, Josh's philosophy is the throughline — the one he repeats to his four kids and to every founder who'll listen:

In our family, we do hard things.

Truth Works is hosted by Jessica Neal, former Chief Talent Officer at Netflix, now in the business of telling the truth about how work really works.

At 11 years old, Dan Mishin convinced his grandmother to move in with his parents so he could turn her apartment into a backpacker hostel. The idea came to him in Berlin, where his mom's wallet had just been stolen and they were stranded overnight in a hostel full of laughing 20-year-olds speaking a language he didn't understand. He made two decisions on the train ride home: learn English, and open a place just like it.

That summer project became the largest hostel chain in Eastern Europe — 13 countries, 3,500 guests a night — and the start of one of the most unlikely founder journeys you'll hear this year.

In this episode, Dan sits down with Jessica Neal to walk through all of it. Starting a company at 11 in post-Soviet Ukraine, a place he describes as the Wild West, with no functioning law enforcement and entire generations of savings wiped out overnight by government decisions. Sleeping in his car for six months when the business almost went bankrupt. Signing 100-year leases with personal guarantees at 18 because Ukrainian law had no concept of bankruptcy protection. Raising a $100M term sheet that same year. Buying a yellow Porsche he now calls a total douchebag move. Ballooning to 280 pounds on a diet of Snickers and Red Bull. And eventually getting on a flight to the US with a single phone number — only to walk away from a 10-minute call with a $100K check at a $5M valuation.

After building Joon Homes to $300M and 250 employees, Dan hit a wall most founders don't talk about: he was building something valuable, but he didn't believe in it anymore. So he walked away to start Manifest — an AI-native legal company that's raised $60M to fix one of the most broken industries in America. The US has 1.3 million lawyers, ten times more per capita than most countries in the world, yet 80% of Americans can't afford one. Dan thinks he knows why, and he's rebuilding the entire system starting with immigration.

The conversation also goes deep on what it actually means to run an AI-native company — how Dan hires, why he believes generalists are winning, the applied AI engineers he embeds in every team, and the one-year severance policy he introduced to take the fear out of automating yourself out of a job.

A conversation about volatility, reinvention, and what it actually takes to build something that matters.

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📌 TOPICS COVERED

▸ Growing up in post-Soviet Crimea and the night in Berlin that started it all
▸ Convincing his grandmother to give up her apartment so he could open a hostel at 11
▸ Building the largest hostel chain in Eastern Europe as a teenager
▸ What it's like to sign 100-year leases at 18 with no bankruptcy protection
▸ Sleeping in his car for 6 months before raising $100M
▸ The yellow Porsche, 280 pounds, and the Snickers-and-Red-Bull years
▸ Landing in the US with one phone number and walking away with a $100K check
▸ Scaling Joon Homes to $300M and 250 employees
▸ Why he walked away from a high-growth business to start Manifest
▸ Why the US has 1.3M lawyers but 80% of Americans can't afford one
▸ How Manifest is rebuilding immigration law with AI from the ground up
▸ Why immigration is a hiring and retention lever most companies underuse
▸ Running an AI-native company: hiring, autonomy, applied AI engineers
▸ Why generalists are beating specialists in the AI era
▸ The 1-year severance policy that made AI adoption psychologically safe
▸ What to do when senior leaders refuse to adapt to AI
▸ His advice to over-thinking founders who won't take real risk
▸ Why this is the most exciting time in history to be building

This week on Truth Works, my co-host Jeff Markowitz and I sit down with Judy Gilbert, the Chief People Officer of Oura, the company behind the Oura Ring.

Judy is not a typical HR leader.

She started her career at McKinsey, moved into executive search at Egon Zehnder, and then spent 12 years inside Google's People Operations team, helping scale the company from roughly 3,000 employees to 70,000.

Along the way she ran learning and development, ran performance management, and served as head of HR for both YouTube and Google's moonshot factory, Google X.

After Google, she became Chief People Officer at the biomanufacturing company Zymergen, where she helped build the team, took the company public, and then navigated its sale and wind-down.

She tried to retire. It didn't last. The pull of being on a team trying to do hard things brought her to Oura.

In this episode, we get into the difference between HR as an order-taker and HR as a genuine strategic partner, and why so many chief people officers get "organ rejected" within a year of joining.

We talk about the danger of arriving with a fixed playbook, the chemistry that has to exist between a founder and their people leader, and why the job is really about being the one person willing to tell the emperor he has no clothes.

Judy also shares the exact questions she asks before taking any role, how she pressure-tested Oura's CEO Tom Hale by sparring with him over compensation philosophy, and why a company's soul has to already exist before anyone can help it grow.

In this conversation, we discuss:

- The "I don't want to know" fear that stops people tracking their health
- Whoop vs Oura, and how much data is actually useful
- Why strategic HR is a competitive advantage most companies waste
- The three questions Judy asks before joining any company
- Why chief people officer turnover is so brutally high
- The "toolkit" mistake that gets HR leaders fired
- Being the person who has to tell the CEO he has no clothes
- Glass balls vs rubber balls, and what to drop when you're building
- How to protect a company's soul while running a hard business
- Why clear cultures keep people and confused ones lose them
- Why every CHRO is now the company's AI strategist

This is a candid look at the work behind the work, from someone who has built the people function at three very different companies and seen what separates the ones that scale from the ones that stall.

If this conversation changed how you think about culture, leadership, or the people who quietly hold a company together, share it with someone who needs to hear it.

Full episode of Truth Works with Judy Gilbert out now.

Chris Voss is the former lead international kidnapping negotiator for the FBI. For seven years, his job was to talk people out of the worst decisions of their lives. He's the reason a bank robber walked out of a Manhattan branch after an eight-hour standoff and surrendered to him personally on the sidewalk. A teammate named Jamie Sedania passed Chris two notes at critical moments. Those two notes ended the standoff.
But Chris didn't start there. He grew up in a small town in Iowa, the son of an entrepreneur who put every kid to work the moment they could carry trash. He joined the Kansas City police, then the FBI, then the New York Joint Terrorist Task Force. He applied for the hostage negotiation team and got rejected. The woman in charge told him to go volunteer on a suicide hotline first. He did. That decision changed everything, because tactical empathy doesn't get built in simulation rooms. It gets built in conversations where the stakes are someone's life.
Today Chris is the founder of the Black Swan Group, named after Nassim Taleb's book on the impact of the highly improbable. He's the author of Never Split The Difference, a book that has sold millions of copies and still ranks #1 in negotiation a decade after release. In this episode of Truth Works, he sits down with Jessica Neal and Peter Clark to unpack how the skills that brought hostages home alive close million-dollar deals, win raises, and transform hiring conversations.
This is not a tactics episode. It's a conversation about what happens inside the human brain when someone feels heard, and why coachability is the rarest and most expensive trait in any room.
What you'll learn:
The 6 second silence rule that triggers oxytocin and serotonin, and why most people destroy it by speaking too soon
Why "negotiate your career, not your salary" is the only raise strategy that actually works, and the exact opening line to use with your boss
The 3 negotiator types (assertive, analyst, accommodator) and how the same silence lands differently with each
How to spot when you're the fool in the game (20% of the time, you are)
Why Stephen Covey got "seek first to understand" wrong, and the small correction Chris makes
The tactical empathy framework, why it was rebranded from plain "empathy," and the neuroscience underneath it
The single observation Chris makes at the grocery store that turns a produce clerk into a personal tour guide
The Robert Greene charmer principle that explains why some people make you feel like the most interesting person in the room
Why coachability is the rarest trait in any room, and the man on a plane who proved it in 10 seconds
The bank robbery story, the swap negotiator tactic, and the two notes that ended an eight-hour standoff
The 22 second silence Elon Musk held with Lex Fridman, and what came out the other side
Learn more about Chris, his Professional Dealmaker Day on May 15th, and his upcoming salary negotiation course at blackswanltd.com.
Truth Works is hosted by Jessica Neal, former Chief Talent Officer at Netflix. New episodes drop weekly. Subscribe for more honest conversations on leadership, work, and what needs to change.

What does it actually take to lead 70,000 people through one of the biggest cultural resets in beauty history?
Michael Bowes, Chief People Officer of The Estée Lauder Companies, joins Jessica Neal on Truth Works for a candid conversation about stepping into the top HR seat at an iconic 80-year-old company in the middle of a billion-dollar restructure, the courage it takes to disagree with your CEO without breaking the partnership, and why the loneliness of the role is real but the work is worth it.
Michael walks through his path from Saks Fifth Avenue in the early 90s, to Nike, to Tommy Hilfiger, to Coach and Tapestry, and a brief detour into executive search before joining Estée Lauder in 2015. He spent almost ten years in talent before being promoted into the Chief People Officer role. He is honest about the fact he was not chasing the title. He took it because he believed in the new CEO Stefan's vision for the next 80 years of the company.
Then the conversation gets into what is actually changing inside Estée Lauder under the new Beauty Reimagined strategy. A culture that used to default to no is now committing to say yes. Over 1,000 different bonus calculations across business units have been consolidated into nine. Brands that used to operate in silos are now rowing in the same direction with one shared set of goals.
Michael also opens up about the realities of the CPO seat that no one prepares you for. The loneliness. The board dynamics. The added complexity of working inside a family-majority-shareholder company. The fact that everyone thinks they can do your HR job until you actually have to do something hard. And the running joke that the only people who tell you they would never want your job are the ones who just watched you do it.
The episode closes with how Estée Lauder is approaching AI as a tool rather than a threat, including how the company is mining 80 years of prestige beauty consumer data in ways no competitor can match. Plus the rise of K-beauty, why Dr. Jart sits inside the portfolio, the China R&D centre that is reversing the old east-to-west flow of trends, and the philosophy that has guided how Michael hires for the last decade: hire the player, not the playbook.
Topics Covered:
How The Estée Lauder Companies scaled from a kitchen in Queens to a global prestige beauty portfolio
Why 87% of the workforce is women and how that shapes consumer decisions
Travel retail as a multi-billion dollar growth channel
Michael's career path from Saks to Nike to Tommy Hilfiger to Coach to Estée Lauder
Being part of the CEO succession conversation before being promoted himself
Taking the Chief People Officer role in the middle of a global billion-dollar restructure
The Beauty Reimagined strategy and its five pillars
Shifting the culture from "protect by saying no" to "we say yes"
Consolidating 1,000+ bonus calculations into nine business units
The loneliness of the CPO seat and why CEO chemistry is non-negotiable
How to disagree with your CEO and still own the decision publicly
Navigating board dynamics and family-majority shareholders
AI as a tool, not a threat, and how Estée Lauder is embedding it across R&D and consumer insight
80 years of prestige beauty data and what AI can unlock from it
The K-beauty wave, Dr. Jart, The Ordinary, and the China R&D centre
The biggest hiring mistake organisations make by default
Why the right hire is the player, not the playbook
The piece of advice from Michael's grandmother that he still lives by
Truth Works is hosted by Jessica Neal, former Chief Talent Officer at Netflix.