Podcast
TruthWorks
Hosted by editaudio · EN
Are you ready to dive deep into the world of work, culture and leadership? Join Jessica Neal and Patty McCord each week as they chat with expert guests and explore the issues affecting the workplace — from AI and mental health, to making layoffs and combating toxic cultures. Featuring global industry leaders and specialists that are passionate about reshaping the way work today. Listen in as we redefine the rules to work for us, not against us. Episode 1 of TruthWorks launches March 19! Subscribe wherever you get your podcasts.
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The CEO Who Saved Homebuyers A Billion Dollars: Why Founder Mode Is A Lie | Glenn Kelman
1w ago00:45:08Tap to summarizeGlenn Kelman ran Redfin for 20 years. He says the most important thing he learned had nothing to do with software.Glenn joins Jessica Neal and co-host Jeff Markowitz on Truth Works for an unusually honest conversation about love, leadership, boards, and the handful of decisions that actually decide a company's fate.Glenn is not your typical tech CEO.At 21 he tried to write a novel, got nowhere, and his girlfriend broke up with him for being unemployed too long. He nearly went to medical school twice. He co-founded Plumtree Software in 1997 and took it public, then almost got fired from the company he started. He joined a nearly dead real estate website that a Seattle VC had put $500,000 into, and spent the next two decades turning it into Redfin, a business that saved consumers roughly a billion dollars in commissions before Rocket acquired it for $1.75 billion.In this episode, Glenn traces the whole thing back to his older brother's struggle with alcohol, the emergency room doctors who kept fighting for a patient any business person would have written off, and the moment he decided he wanted to be good like that.He is candid about the parts most CEOs edit out. The board meeting where he quoted Yeats and Colonel Jessup from A Few Good Men. The walk with a Greylock partner that reset his entire relationship with his board. The rentals acquisition he financed with debt in 2021, right before the music stopped. Rewriting a single email 83 times because he could not figure out how to disagree with his new parent company's CEO.Jeff and Jessica bring two decades of executive search experience to the hiring question Glenn admits he never fully solved, including the advice from Jeff that gave Glenn permission to walk away from a candidate he had already taken to dinner, drinks, and references.━━━━━━━━━━━━━━━━━━━━━━TOPICS COVEREDFINDING THE WORK→ Why writing alone in a room made him depressed, and why business is just being creative with other people→ Working for three founders barely older than him and realising he could do it too→ Picking the big idea over the small one, and why ambition makes recruiting easier→ His brother's addiction, the ER doctors, and the decision to do something good inside businessHIRING AND JUDGEMENT→ Jeff's method: go in looking for every reason the person is wrong→ Never hiring someone you are not genuinely excited about, even when you have come too far to stop→ What negotiating severance reveals about a candidate before they start→ Why subjectivity is a feature, not a bug, and the Peter Chernin story behind itBOARDS AND CEO GROWTH→ How a fraught, adversarial board became one of his greatest assets→ Blaming the board when the real problem is the product→ The one question that turns a board meeting from a performance into a working session→ Why $50M seed rounds at $400M valuations have made honest board conversations harderLEADERSHIP AND THE HARD CONVERSATION→ Being too kind for too long, and the cost of hints instead of clarity→ Writing down what you need to say, then throwing the paper away and saying it anyway→ Getting nearly fired at Plumtree in a 30-second conversation, and the turnaround that followed→ Why founder mode has a real insight buried inside a bad excuse→ Making the call people disagree with, then calling them afterwards to replay their argument backWHAT HE ACTUALLY LEARNED→ Working 15-hour days when four or five one-minute decisions created more value than all of them→ Why he stopped trying to be the smartest person in the room→ Real estate agents, a sea of love, and how they changed how he sees business→ His closing gift to listeners: if people feel the love, they will forgive almost anything━━━━━━━━━━━━━━━━━━━━━━Subscribe for more honest conversations with the people who have actually built things.
Transcribe →$40B Canva CHRO: How Canva Actually Builds Culture & Why they open source their Playbooks!
2w ago00:56:26Tap to summarizeWhat does it actually take to build the people function at a company that went from a design tool to a global platform of 5,500 people?Jennie Rogerson, Chief People Officer at Canva, joins Jessica Neal and co-host Peter Clarke on Truth Works for a conversation about culture as an operating system, not a perk.Jennie's path into the role is one of the more unlikely ones in tech. She came up through hospitality, running restaurant floors where 220 covers a night meant 220 individual experiences to manage. She moved into hospitality tech, then got dragged to an after-work Canva workshop on making better presentations — and walked out convinced she had to work there.She applied. She didn't get the jobs. A colleague told her to look elsewhere. She ignored the advice.When the executive assistant role for co-founders Melanie Perkins and Cliff Obrecht opened up, thousands of people applied, and Jennie had no experience in the domain. So instead of a resume, she built a website. Canva launched Canva Websites the night before she planned to send it, so she rebuilt the entire thing on the product overnight. Then she spotted a line in Cliff's LinkedIn bio — "you're great, we're hiring" — and sent it to him directly.The interview process was two live challenges and a lot of real-time pushback. By the end of it, the role had been rewritten into something new: Leadership Operations, a chief-of-staff seat between the founders and the leadership team. Eighteen months later, Cliff called on a Sunday to offer her the top people job. Her first response was to ask if he'd lost his mind. She took it as an interim role. It's been years.Jennie is refreshingly clear that Canva hasn't figured everything out, especially around parental leave re-onboarding, which she says most companies get wrong and hers is still actively learning. But what they have built is worth studying: managers are called coaches, performance reviews are called Growth and Impact, and every employee can anonymously submit to the Fix It Form, which has been running for roughly eight years and asks two questions — what's broken, and what's your solution.The conversation also gets into the support playbooks Canva built for grief and loss, family and domestic violence, and cancer and long illness — written with the employees who lived through those moments, and then open-sourced so any company can use them. One of them started as a single Fix It Form submission from someone who had lost their wife.And on hiring: Canva's CMO started as a communications intern. One of their AI researchers was found on a Discord community while he was stocking supermarket shelves. Those sit alongside senior hires from Zoom, Uber and Google — because the blend is where the value is.TOPICS COVERED:- Why hospitality is underrated training for building a people function- Getting hired with a website instead of a resume- The interview challenge that turned into a brand new role- Being offered the top people job with no HR background- Why culture is everyone's accountability, not the people team's- The Fix It Form — anonymous, always on, and it requires a solution- Why Canva calls managers "coaches" and reviews "Growth and Impact"- What a performance cycle looks like when it isn't a box-ticking exercise- Season openers and building public accountability into the calendar- Parental leave re-onboarding and why nobody has solved it yet- Building and open-sourcing the Grief and Loss guide- Talking about family and domestic violence at work- The risk of not talking about hard things- Finding talent internally and hiring for curiosity over pedigree- Using AI to draft the process, then keeping humans in the loopMost of this episode comes back to one idea. Jennie was hired into a role she was unqualified for on paper, by people who were looking for something other than a track record. Everything she has built since runs on the same logic — the AI researcher on Discord, the intern who became CMO, the engineers she invites to tear apart her own processes because they're the ones actually living inside them.Her closing challenge cuts both ways. If you're running an organization, the person who could take the next big step is probably already inside it, waiting for someone to bet on them. And if you're the one looking for what's next, the most interesting move might not be the logical one on paper — it might be the thing you're genuinely curious about.Which is why the line she keeps returning to isn't really about Canva at all:You don't join Canva to experience the culture. You join Canva to be the culture.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.
Transcribe →He 2x'd Instagram's valuation in 3 Days: Why Nothing About AI Is Settled Yet || John Lilly
3w ago00:43:25Tap to summarizeJohn Lilly has had a front row seat to almost every major shift in technology over the last thirty years, and he has sat in almost every chair while it happened.He was a Senior Scientist at Apple in 1997, when the market cap was two billion dollars and most people assumed the company was finished. He co-founded Reactivity, later acquired by Cisco. He became CEO of Mozilla and led Firefox past 450 million users, running an open source nonprofit at a time when nobody else in Silicon Valley was doing anything like it. Then he spent over a decade as a General Partner at Greylock, where he led investments in Instagram, Dropbox, Figma, Tumblr and Quip. He sits on the boards of Figma, Duolingo and Nuro, and recently joined Gigascale Capital as an Advising Partner, backing companies rebuilding the physical economy.In this conversation with Jessica Neal and co-host Jeff Markowitz, John walks through what he actually saw in the founders everyone else missed.He tells the story of chasing Kevin Systrom for six months, wiring the money on a Thursday, and getting the call three days later that Instagram was selling to Facebook. He explains the moment a friend showed him Instagram and what clicked was not the filters, it was the distribution. And he describes meeting a 19 year old Dylan Field at a Starbucks in Palo Alto, telling him his product did not matter, and then spending the next decade watching him prove it wrong.He is also honest about the parts that are harder to hear. Why some partners at Greylock wanted Dylan replaced. Why he thinks micromanaging the right things is a feature of good leadership, not a flaw. Why he does not tell CEOs anything, and what he does instead. And why, at a moment when OpenAI and Anthropic are pulling talent out of every company on earth, the answer is not matching the money.He closes with something a colleague at Mozilla told him years ago that he still carries: we had a chance to make the world we wanted, and we did it.━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━WHAT WE COVER━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━THE FOUNDER QUESTION→ How John spotted Dylan Field at 19→ Why recruiting senior people is the strongest early signal→ The trait every great founder shares: relentless about getting help→ Why non-defensiveness beats raw intelligence→ The lunch where they told Dylan he had to build a go to marketTHE INVESTMENTS→ Chasing Kevin Systrom for six months→ The underwater photographer who explained Instagram to him→ Why the network mattered and the filters did not→ The four day flip to Facebook and what he told his LPs→ The Adobe Killers that came before Figma and why this one was differentLEADERSHIP AND SCALE→ Going from 12 people to a quarter of the internet at Mozilla→ Why he never learned the delegation lesson everyone teaches→ Larry and Sergey reviewing every resume and what that signals→ Learning to be simpler in your message as you grow→ Deciding you would rather be successful than comfortableTHE TALENT WAR→ Why every great person is now a free agent→ The spreadsheet exercise he gives every CEO→ Tour of duty and the bilateral deal between company and employee→ Never making an offer until you know it will be accepted→ Why money is rarely the only reason people leaveTHE CURRENT MOMENT→ Why leadership now means stability without pretending anything is stable→ The collision of faster scaling and total vulnerability→ Why org size no longer scales with impact→ Alpha nerds, Tim O'Reilly, and following the most technical people around→ Investing in transformers, copper recycling and rare earth supply chains→ Why none of the AI future is settled and it is all still to play for━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━CONNECT WITH JOHN LILLYLinkedIn: linkedin.com/in/johnlilly━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━Truth Works is hosted by Jessica Neal, former Chief Talent Officer at Netflix, with co-host Jeff Markowitz.
Transcribe →What Netflix got Right and Why Most companies are built WRONG for AI! - Dr. Mik Kersten
4w ago00:48:50Tap to summarizeWhat if your teams became 10x more productive — and your business got nothing out of it?Dr. Mik Kersten has the data to prove it's already happening. After studying more than 8,000 value streams across enterprises, he found that only 8% of end-to-end delivery time is teams actually creating value. The rest disappears into planning, approvals, reviews, and coordination. Which means you can multiply team productivity by 2x or 10x with AI, and deliver nothing faster to your customers.Mik started his career as a research scientist at Xerox PARC, completed his PhD in Computer Science, and founded Tasktop, which he led as CEO until its acquisition by Planview in 2022. He's the creator of the Flow Framework and the bestselling author of Project to Product. His new book, Output to Outcome: An Operating Model for the Age of AI, launches July 14, and it argues that the constraint on knowledge work is gone. What's left is your organizational structure. And for most companies, it's the thing standing in the way.In this episode, Mik joins Jessica Neal and co-host Peter Clarke to break down why AI productivity gains aren't showing up in business results, what happens to companies that spend big on tokens without rewiring how they work, and why the future of leadership means every manager becomes a maker again.You'll learn:- Why only 8% of enterprise delivery time is actual value creation — and where the other 92% goes- Why 10x team productivity means nothing if your organization can't absorb it- The four competing structures inside most companies: org chart, value streams, incentives, and architecture- What Netflix got right about aligning technology, teams, and leadership- The "outcome tree": one unified structure replacing the matrix- Why humans should keep reporting to humans — even as agents join teams- How incentives quietly sabotage transformation (and why Mik wrote half a chapter on them)- Why outputs are easier to measure than outcomes — and why that's now a fatal trap- The dark factory thought experiment: what happens when production cost trends toward the price of electricity- Zero bonuses for engineers: what Mik learned from the experiment- Why planning still matters — but on weekly and monthly cadences, not annual- Managers to makers: why the first-line manager role is changing completely- The middle managers whose roles are gone — and the new role that replaces them- Why companies that get this right are hiring more people, not fewerMik's message to leaders: get hands-on with the latest models now. The only way to make AI work for your teams — instead of the other way around — is to lean in.Output to Outcome: An Operating Model for the Age of AI is available now wherever books are sold.Truth Works is hosted by Jessica Neal, former Chief Talent Officer at Netflix.
Transcribe →Google, Shopify..."Stay Away From The Badge Hunters": The Hiring Rule That Built Public.com
Jul 700:54:10Tap to summarizeEverything breaks in a startup. Culture is what kicks in when it does.Leif Abraham and Jannick Malling are the co-founders and co-CEOs of Public, the agentic brokerage putting AI agents to work directly inside your portfolio. They started in late 2019 by bringing their two former teams back together, and have since watched every market cycle twice: from launch, to the GameStop chaos of January 2021, to the AI shift they're now building on top of.In this episode, they sit down with Jessica Neal and Peter Clarke to unpack how they actually run the company. They break down their 10 open-sourced operating principles ("Honesty kills bullshit," "Find a way," "Move fast through organised speeding"), why they treat culture as capitalistic tooling rather than fluffy values, and the moment Principle 10 drove a small engineering team to scale the trading system overnight when GameStop doubled their user base in a week, a decision that still compounds into Public's reputation for uptime today.They also make the case for the co-CEO model most investors say never works. The trick, they argue, is that they don't share a job, only a title: Jannick lives inside product and engineering, Leif runs growth, and they only converge on the 1% of existential decisions where more perspectives actually matter. It lets them stay deep in their craft and install one C-level hire at a time instead of scaling leadership in risky staircases.On hiring, they get pointed. Avoid the "badge hunters" who collect logos and optimise their LinkedIn, and instead find people who had to fight for their growth at companies you've never heard of. Be "truth-seeking to an uncomfortable degree" in interviews, because technical ability is table stakes, but motivation is the thing that actually predicts fit.Plus Jannick shares how he generates 20K a month selling covered calls, why AI agents are about to compress trading strategies into a single prompt, and how the pair are betting the next decade of investing will be about resourcing individuals, not just granting them access.00:00 Intro02:00 What Public is: the agentic brokerage06:00 Selling covered calls on autopilot11:00 Access vs resources: the next 10 years of investing16:00 Building culture from two merged teams20:00 Principle 1: Honesty kills bullshit27:00 Culture as the operating system, principles as the tools33:00 The GameStop scaling story and Principle 1039:00 Making the co-CEO model actually work48:00 Disagreement as a feature, not a bug53:00 Hiring: stay away from the badge hunters1:00:00 Truth-seeking in interviews1:05:00 Closing: problems, purpose, and health firstThis episode is not investment advice.#TruthWorks #Public #Investing #AgenticAI #Startups #Founders #CoCEO
Transcribe →The Modern-Day Napoleon Hill: Why Most People Don't Believe in Themselves! Evan Carmichael
Jun 3000:52:29Tap to summarizeEvan Carmichael believes the world's biggest problem is that people don't believe in themselves enough. He has spent the last 15 years trying to fix it.Evan joins Jessica Neal and co-host Jeff on Truth Works for an honest conversation about self-belief, building a movement as an introvert, and why serving one person matters more than reaching millions.Evan is not your typical YouTuber.At 19 he built and sold a biotech software company. At 22 he was a venture capitalist raising $500k to $15M. Then he started making videos on YouTube in 2009, long before entrepreneurs were a category there, and for five years almost nobody watched. His first year online he had three comments, two of them from his own family.Today his #Believe channel has over 4 million subscribers, he has written four books, and Ed Mylett has called him the modern-day Napoleon Hill.In this episode, Evan breaks down the "believe walk" he does every morning, why he thinks your purpose comes from your pain, and how a mentor named Steve pushed him from 9,000 subscribers to millions by making him film the same foundation story 40 times. He gets candid about the hardest day of his life, the one day in 15 years he could not bring himself to turn on the camera, and what it taught him about being human.He also shares the systems behind the work: the eliminate, automate, delegate framework, why he themes every day of his week, and the "CEO day" he uses to make the calls he keeps avoiding. Plus why he leads his 60-person team with directness rooted in love, the difference between pushing someone and hugging them, and how to know which one a person needs.TOPICS COVERED- Why lack of belief is the world's number one problem- The "believe walk" and curating what goes into your head every morning- How an introvert built a movement without wanting to be famous- Why your purpose comes from your pain- The five-year grind from 0 to a couple thousand subscribers- Asking for help and why most people wait too long to do it- Big Y vs little Y: staying motivated by serving one person- Why successful entrepreneurs take action immediately- Eliminate, automate, delegate: scaling yourself out of the work- Theming your week and the "CEO day" thought exercise- Leading with love: when to push someone and when to hug themEvan's books, including Your One Word and Built to Serve, are available now.Truth Works is hosted by Jessica Neal and Jeff, two leaders pulling back the curtain on how great companies and people are really built.
Transcribe →"AI Is Quietly Killing Your Curiosity! - No.1 Coaching Expert | Michael Bungay Stanier
Jun 2300:50:59Tap to summarizeWhat if AI is quietly making you a worse leader, and you can't even feel it happening?Michael Bungay Stanier (MBS) is the bestselling author of The Coaching Habit, one of the most widely read leadership books of the last decade, now re-released in a 10-year anniversary edition. He is the founder of Box of Crayons and the host of the Change Signal podcast.In this episode of Truth Works, he joins Jessica Neal and guest co-host Peter Clarke to ask an uncomfortable question: is AI making us worse leaders?His answer is yes.━━━━━━━━━━━━━━━━━━━━━━THE CORE ARGUMENTAI seduces us into speed, certainty, and the half-decent answer, at the exact moment leadership demands the opposite. MBS argues curiosity is being chipped away in all of us, and the leaders who survive the AI era will treat it as a discipline they practice, not a trait they assume they have.At the center of the conversation is his framework for what leadership now requires:→ Clarity over certainty→ Context over content→ Connection over cocooning→ Courage over collusionHe and Jessica unpack why judgment and taste, not big teams, budgets, or functional expertise, are the skills that actually scale when everyone has the same information and the same tools.━━━━━━━━━━━━━━━━━━━━━━INSIDE NETFLIXJessica draws on her years at Netflix, where the company interviewed for curiosity, treated big decisions as "bets" instead of life-or-death calls, and reframed failure as data.She tells the story of the $100M House of Cards bet, admits most of Netflix's decisions were actually bad ones, and explains how a culture of small experiments and honest trade-offs is what let the company take the swings that built it.━━━━━━━━━━━━━━━━━━━━━━ALSO IN THIS EPISODE→ Why data is political, not neutral→ Why courage is the real differentiator behind every great founder→ The strategy question: "If we say yes to this, what must we say no to?"→ The deeper gift of coaching that has nothing to do with having the answer: helping people feel seen, heard, and encouraged━━━━━━━━━━━━━━━━━━━━━━TOPICS COVERED→ Why AI is deadening curiosity more than fostering it→ The 4 C's of leadership in the AI era→ Why judgment and taste beat big teams and budgets→ The Netflix $100M House of Cards bet→ Why most of Netflix's decisions were bad ones, and why that was fine→ Building a culture of small experiments→ Why data is political, not neutral→ Why courage is the differentiator behind every great founder→ The strategy question→ The deeper gift of coaching━━━━━━━━━━━━━━━━━━━━━━Find Michael: MBS.works | boxofcrayons.com | The Coaching Habit (Amazon)Truth Works is hosted by Jessica Neal & Peter Clarke.
Transcribe →Stanford Professor: Why 85% of People Freeze Up while speaking and 15% might be Lying!
Jun 1600:40:11Tap to summarizeThe Communication Expert: The No.1 Skill AI Can't Replace | Matt AbrahamsMatt Abrahams has spent nearly two decades teaching the one skill almost no one is formally trained in: how to communicate. He's a lecturer in Strategic Communication at Stanford's Graduate School of Business, the bestselling author of "Think Faster, Talk Smarter" and "Speaking Up Without Freaking Out," and the host of the "Think Fast, Talk Smart" podcast.In a world racing toward AI, Matt makes a counterintuitive case: the more capable our machines become, the more our human ability to connect, persuade, and be understood will decide who thrives and who gets left behind.In this episode, Jessica Neal and Jeff Marquitz sit down with Matt to unpack the science and the practice of communication. They get into the "authenticity crisis" and the "empathy paradox" emerging as we hand our hardest conversations to AI, why up to 85% of people freeze in high-stakes moments, and the exact, repeatable techniques to manage that anxiety in real time.Matt doesn't speak in abstractions. He breaks communication down into mindset and messaging, shares the only three ways anyone actually gets good at it, and walks through how to build a personal "anxiety management plan" you can use before your next big meeting or talk. He also explains why most companies treat communication as an afterthought, and how founders can turn it into a genuine competitive advantage.If you've ever gone silent in a room full of people who intimidate you, or felt your body betray you on stage, this conversation is a practical playbook for showing up clearer, calmer, and more human.————————————————————TOPICS COVERED– Why AI makes human connection more important, not less– The "authenticity crisis": when perfect words stop feeling like yours– The "empathy paradox" and the risk of empathy atrophy– The evolutionary reason public speaking terrifies us– The three sources of speaking anxiety: audience, situation, and goal– Physical techniques to calm nerves in the moment– The only three ways to get good at communication: repetition, reflection, feedback– How to build your own anxiety management plan– Why communication should be taught in schools and modeled at work– Mindset and messaging: why you can't separate the two– Building a "communication infrastructure" inside a company– Why "getting it out" is not the same as being understood– Giving vs. getting: how the goal changes the conversation– Matt's nightly journaling practice for improving over time————————————————————
Transcribe →Fortune 500 work with this CEO building a $1billion dollar company with 100 people - Siobhan Savage.
Jun 900:50:17Tap to summarizeWhat if the reason the world's biggest companies keep failing at AI has nothing to do with the AI itself?Siobhan Savage is the co-founder and CEO of Reejig, the Work Operating System helping the most complex organizations on earth move work to worker in the age of AI. She works with Fortune 500 companies across banking, pharmaceutical, and retail, and she is building a billion-dollar company on a single conviction:opportunity belongs to the builder, not the platform.━━━━━━━━━━━━━━━━━━━━━━HER STORYOne of twelve children. Canadian born, Irish raised, 15 years in Sydney, now in New York. She built her career in workforce strategy on multi billion dollar projects, obsessing over one question: how do you move work to the right worker and make a business run at high velocity?She never imagined agents would become a form of worker. Now that future is arriving, and the Fortune 500 calls her to make sense of it.━━━━━━━━━━━━━━━━━━━━━━WHAT THIS EPISODE EXPOSESIn this episode of Truth Works, Jessica Neal and co-host Jeff Markowitz sit down with Siobhan to reveal what is really happening inside enterprise AI.Most large companies have turned AI into transformation theatre: 12 month programs, enormous consulting bills, prompt training that changes nothing, and tools that get switched on then quietly switched off when the ROI never shows up.The problem is not the technology. It is that almost no one has actually looked at how the work runs.Reejig spent $40 million mapping how work actually works, building a view of tasks, subtasks, and skills before large language models were even real. That map is why Siobhan can walk into a company and understand 80% of its work without touching a single system.She also draws a hard line on responsibility. Being Bold AND Responsible is not a slogan for her, and she refuses to design a world where two iPads interview each other in a boardroom.Then it gets personal: raising "baby builders," the mom guilt of 16 hour days, and the human skills she believes will matter most in the careers of the future.━━━━━━━━━━━━━━━━━━━━━━TOPICS COVEREDTHE BACKSTORY→ One of twelve children, Canadian born, Irish raised, 15 years in Sydney→ Starting out in workforce strategy and the obsession with moving work to worker→ Recruiting as the ultimate training ground for resilience and connectionTHE ENTERPRISE AI REALITY→ The real reason enterprise AI is failing, and why it is not the AI→ Transformation theatre: long programs, consulting bills, prompt training that changes nothing→ Why tools get switched on then switched off when the ROI never appears→ Making invisible work visible without plugging into emails or calendars→ How Reejig spent $40 million mapping work before large language models were real→ Understanding 80% of a company's work without touching a single systemVALUE OVER COST→ The shift from cutting cost to unlocking value and growing margin→ How an invoice that took five hours can be reduced to 45 minutes→ Why your job is made of tasks, and how AI quietly removes parts of them→ Emerging and declining skills, and the danger of "jobs of the future" courses→ Stealth change management and the iPhone upgrade approach to adoptionTHE BIGGER QUESTIONS→ What it means to be Bold AND Responsible when jobs are on the line→ The leaders harvesting people out of jobs while paying consultants millions→ How the CHRO role is about to fundamentally change→ Managing a workforce of both humans and agents→ The handcrafted human experience making a comeback, even at AI companiesTHE PERSONAL SIDE→ Raising "baby builders" and teaching kids to use AI early→ Why human to human skills become more valuable, not less→ Mom guilt, 16 hour days, and choosing to build→ Why opportunity belongs to the builder, Jane in accounts, not just the PhDs━━━━━━━━━━━━━━━━━━━━━━This is a conversation for anyone trying to understand what work becomes next, whether you lead a Fortune 500 company or you are figuring out your own place in the AI era.━━━━━━━━━━━━━━━━━━━━━━Guest: Siobhan Savage, co-founder and CEO of ReejigHosts: Jessica Neal and Jeff Markowitz
Transcribe →$10B Gusto CEO: "Imagine Describing Your Idea The 10,000th Time, Will You Still Be Excited?"
Jun 200:49:55Tap to summarizeThree 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.
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