#485 Chris Schembra - Inviting Strangers To Your Apartment Might Be The Solution To Loneliness

If you’re struggling to close deals, join the Sales Skills For Founders newsletter here: 📨 https://salesskillsforfounders.comSummary:In this solo episode, I share my personal journey of leaving corporate America after 15 years in software sales to build my own sales coaching business. I walk through the path that got me here, from a former golf pro to a top performing seller to a founder, and I break down the two to three years of preparation that made the jump possible. I cover five key lessons: building momentum before you quit, focusing on doing better instead of doing more, giving yourself permission to act, ditching the idea that there's one right playbook, and finding your circle of peers, mentors, and coaches. You'll walk away with a practical, honest framework for thinking through your own transition out of a stable job, including how to think about branding, getting paid clients early, and getting your finances in order before making the leap.Chapters:0:00 Intro / Welcome back1:01 My backstory: from golf pro to corporate sales3:06 The 2019 conference that planted the seed4:15 Coffee chats with Doug that turned into coaching5:28 The question from Randy that changed my direction6:06 How the idea came together in early 20247:11 Point 1: Create momentum before you jump8:01 Build your brand before you need it10:02 Get paying clients before you go full time11:39 Get your finances in order first14:57 Point 2: Don't do more, focus on better16:33 Point 3: You don't need permission18:49 Point 4: There is no playbook, write your own21:41 Point 5: Find your people, peers, mentors, coaches26:19 Final thoughts and how to connect with me👋 Hey, I'm Brian Ondrako and I left a 15-year career as a top performing software sales rep to coach early-stage startups on the skills and systems to build predictable revenue. Check out my coaching programs on my website, https://brianondrako.com or say hello on LinkedIn, https://www.linkedin.com/in/brianondrako/

Sign-up for the free Sales Skills For Founders newsletter: https://salesskillsforfounders.com/Most startup founders set an annual revenue goal and then hope for the best. In this video, I break down a simple but powerful framework for working backwards from your number so you always know exactly where you stand.This can be the difference between hitting your number and scrambling at year-end. Whether you're early in your sales journey or trying to add more predictability to your revenue, this math-first approach will change how you think about your pipeline.Chapters:00:00 Why Startup Founders Struggle With Predictable Revenue01:18 Setting an Annual Target and Breaking It Into Halves and Quarters02:45 Going Monthly and Why Smaller Chunks Keep You on Track04:20 Pipeline Coverage and Why You Need 3-4X Your Revenue Goal06:10 Running the Real Numbers on Deals and Pipeline Size08:30 Three Takeaways: Know Your Number, Break It Down, Build Coverage10:45 Diversify Your Pipeline and Stay Accountable Week Over Week👋 Hey, I'm Brian Ondrako and I left a 15-year career as a top performing software sales rep to coach early-stage startups on the skills and systems to build predictable revenue.Check out my coaching programs on my website, [https://brianondrako.com](https://brianondrako.com/) or say hello on LinkedIn, https://www.linkedin.com/in/brianondrako/

Stan Phelps and David Rendall are co-authors of Speak Different, a book built for executives and entrepreneurs who already present regularly and want to take their skills to a higher level. Stan has written 20 books and is one of only two people in the world holding three earned speaking distinctions simultaneously. David has spoken in 32 countries and built his entire speaking career on one core idea: what makes you different is what makes you powerful.In this episode, you will walk away knowing why nervous energy before a presentation is actually your greatest asset, how to build a story bank you can draw from in any room, why the single idea constraint is what separates forgettable presentations from ones people quote years later, and how a simple four-part framework called QQSS can transform how you communicate whether you are on a stage or sitting at a conference table.Chapters:0:00 - Welcome Back and the 3,036-Day Gap3:04 - Book Launch Philosophy and Playing the Long Game9:05 - The 80 Percent Stat That Stops Rooms Cold11:40 - Anxiety Is Energy, Not the Enemy14:15 - The Bahrain Story and Why Public Speaking Isn't That Different22:15 - Malcolm Gladwell and the Power of a Single Story25:34 - Introducing QQSS: Quotes, Questions, Stories, and Statistics32:01 - Hope Stories vs. Fear Stories37:55 - The Story Bank: Your Secret Weapon in Any Room43:50 - What to Do Today to Get One Step Ahead52:05 - How Stan Prepares Before Walking Into Any Room57:27 - Final Thoughts and the One Idea That Runs the Whole BookFind Stan & David Online:Stan Phelps - https://stanphelps.com/David Rendall - https://www.drendall.com/ Speak Different Book: https://a.co/d/0hVm3zuW Say Hello To Your Host:👋 Hey, I'm Brian Ondrako and I left a 15-year career as a top performing software sales rep to coach early-stage startups on the skills and systems to build predictable revenue. Check out my coaching programs on my website, https://brianondrako.com or say hello on LinkedIn, https://www.linkedin.com/in/brianondrako/If you’re struggling to close deals, join the Sales Skills For Founders newsletter here: 📨 ⁠https://salesskillsforfounders.com

Eric Ries changed how a generation of founders build companies with The Lean Startup. Now he is back with Incorruptible, a blueprint for making sure the company you build never betrays the mission that made it worth building in the first place. In this episode, Eric breaks down the invisible force he calls financial gravity, the force that quietly pulls even the most well-intentioned companies toward short-term thinking and eventual corruption. You will hear the real story behind building the Long-Term Stock Exchange, why only 20% of venture-backed founders are still CEO three years after an IPO, and the one two-page legal filing that could protect everything you are building. If you are a founder, an operator, or anyone who cares about doing business the right way, this conversation will change how you think about building for the long term.Chapters:0:00 - Eric Ries on Building Companies That Never Lose Their Soul 1:22 - Did Eric Know The Lean Startup Would Change the World? 3:17 - The Origin of the Title of His New Book, "Incorruptible"5:30 - Rapid Fire #1: Most Humbling Setback as a Founder 6:07 - Rapid Fire #2: How Do You Decide What Is a Priority When Everything Feels Urgent 11:10 - Rapid Fire #3: How Do You Decide What to Track With KPIs 14:47 - Rapid Fire #4: The One Tool You Cannot Live Without 16:40 - Rapid Fire #5: When Did You Last Want to Give Up But Did Not 18:26 - Why Eric Finally Wrote "Incorruptible" 22:49 - Why Corporate Corruption Is Getting Worse Not Better 26:52 - Value Destroying vs. Value Creating: The Sol Price and Costco Story 36:25 - How Founders Avoid Becoming Corrupt as They Scale 40:06 - The One Action Every Founder Should Take Today 45:30 - What Got Cut from the Book and Where to Find It 47:22 - Where to Find Eric Ries and How to Get Incorruptiblehttps://www.incorruptible.co/Linkedin: https://www.linkedin.com/in/eries/X: https://x.com/ericriesInstagram: https://www.instagram.com/ericriesactual/TikTok: https://www.tiktok.com/@ericriesactualNewsletter: https://news.theleanstartup.com/Podcast: https://www.youtube.com/@theericriesshow or https://www.ericriesshow.com/👋It’s your host, Brian! Come say hi!Website: https://brianondrako.comLinkedIn: https://www.linkedin.com/in/brianondrako/ Youtube: https://www.youtube.com/@brianondrako Or, if you’re struggling with sales, join the Sales Skills For Founders newsletter and learn how to lead better sales conversations, spot weak deals early, and build a pipeline you can actually trust. 📨 https://salesskillsforfounders.com

Deb Liu has spent over two decades at the center of tech's biggest moments including PayPal's IPO, Facebook Marketplace, and four years as CEO of Ancestry. Now she's back as co-founder of Ember AI, building enterprise workflow automation at a moment when everything is moving faster than ever. In this episode, Deb gets honest about the career setbacks that almost pushed her out of tech, the personal losses that forced her to pause, and why she couldn't sit out the AI revolution. You'll walk away with practical thinking on how to say no without guilt, how to build teams that never get stuck, why "creator vs. consumer" is the most important distinction for the next generation, and how AI will reshape the way we all develop judgment and expertise at work.Chapters:0:00 How Deb Liu Went from PayPal and Meta to Founding an AI Startup2:30 How Generative AI Arrived Faster Than Anyone in Tech Predicted3:45 Rapid Fire Q1 - What to Do When Things Get Hard6:10 Rapid Fire Q2 - How to Know When to Say Yes or No to Opportunities7:30 Rapid Fire Q3 - How to Stay Motivated When Results Are Slow to Come 9:05 Rapid Fire Q4 - How Introverts Can Learn to Speak Up and Lead at Work 12:00 Rapid Fire Q5 - How Taking a Risk at PayPal Changed Deb Liu's Entire Career13:45 How to Build a Startup Team Culture That Stays Unblocked and Moves Fast18:50 How AI Is Changing Entry-Level Jobs and What the Workforce Needs to Do About It23:15 How to Help Kids Become Creators in a World Built for Consumers26:35 How Ember AI Helps Companies Automate Without Needing Software Engineers35:55 How AI Can Expand Access to Therapy, Education, and Opportunity at ScaleFind Deb OnlineWebsite: https://debliu.com/ Linkedin: https://www.linkedin.com/in/deborahliu/⁠ Substack: https://debliu.substack.com/ Ember AI: https://ember.new/👋It’s your host, Brian! Come say hi!Website: https://brianondrako.comLinkedIn: https://www.linkedin.com/in/brianondrako/ Youtube: https://www.youtube.com/@brianondrako Or, if you’re struggling with sales, join the Sales Skills For Founders newsletter and learn how to lead better sales conversations, spot weak deals early, and build a pipeline you can actually trust.📨 https://salesskillsforfounders.com

Charlene Li is a New York Times bestselling author of seven books, founder of Altimeter, and CEO of Quantum Networks Group. A Harvard graduate and globally recognized expert on digital transformation and disruptive leadership, she has advised 49 of the Fortune 100 and spoken at the World Economic Forum, TED, and SXSW. Her latest book, "Winning with AI: The 90-Day Blueprint for Success," gives leaders a practical framework for creating real business value with AI, not just experimenting with it. In this episode, Charlene breaks down the difference between predictive, generative, and agentic AI, shares why AI is a leadership problem first and a technology problem second, and gives founders a concrete path to going from AI-curious to AI-fluent in just 90 days. If you want to stop dabbling and start winning with AI, this episode is your starting point.Chapters:0:00 Welcome Back and Charlene's New Book Launch0:36 Charlene's Background and the Leadership Thread Through All Seven Books1:25 Defining AI, Generative AI, and Agentic AI in Plain Language3:02 What a Founder's Work Week Could Look Like With Agentic AI6:35 Does AI Scare You? Charlene's Honest and Balanced Take8:06 The Five Human Traits AI Will Never Replace11:24 Why Gen Z Is More Skeptical About AI Than Boomers and Gen X15:32 What the 13% of Companies Actually Winning With AI Do Differently19:14 Strategy First: Stop Asking What AI Can Do, Ask How It Helps You Win22:43 Why AI Fluency Is a Leadership Problem, Not a Technology Problem27:55 The One Prompt Trick That Transforms How You Work With AI32:36 Which AI Tools Charlene Actually Uses Every Day38:57 How to Stay Current When Everything Is Changing and Where to Find Charlene:Website: https://charleneli.com Linkedin: linkedin.com/in/charleneliYoutube: youtube.com/charleneliWinning With AI book: winningwithaibook.com👋It’s your host, Brian! Come say hi!Website: https://brianondrako.comLinkedIn: https://www.linkedin.com/in/brianondrako/ Youtube: https://www.youtube.com/@brianondrako Or, if you’re struggling with sales, join the Sales Skills For Founders newsletter and learn how to lead better sales conversations, spot weak deals early, and build a pipeline you can actually trust.📨 https://salesskillsforfounders.com

Chris Schembra is a Wall Street Journal bestselling author, gratitude strategist, and founder of the 747 Club — a dinner party experience that has brought together tens of thousands of people across the globe. In this episode, Chris takes us back to July 15, 2015, the night he invited 15 strangers to his 300-square-foot Manhattan apartment, made a simple pasta sauce, and asked one question that changed everything: "Who have you never thought to thank?" What emerged wasn't just a dinner — it was a movement. Chris breaks down the concept of "designed friction" and why our obsession with frictionless connection has made us lonelier than ever. You'll walk away with three actionable pillars — presence, intimacy, and coherence — to start building more meaningful relationships starting today.Find Chris Online:Website: ⁠http://www.chrisschembra.com/⁠Linkedin: ⁠https://www.linkedin.com/in/schembra/⁠Chapters:0:00 — Welcome & Chris Challenges Brian to Do the Opposite1:39 — July 15th, 2015: Brian Sets Up the Origin Story2:44 — Chris Begins: Life Before the Dinner Party4:41 — The Moment in Rome That Changed Everything6:01 — From Murphy Bed to Pasta Sauce7:37 — The First Dinner and the 7:47 Gratitude Question9:04 — How Chris Got 15 Strangers to Show Up10:41 — How the Gratitude Question Was Born14:36 — How to Reconnect When Most People Won't Even Send a Text20:48 — The League of Gentlemen: How a Breakfast Became a Brotherhood28:12 — Virtual vs. Real: Hybrid Is How We Connect29:40 — Frictionless Design Has Left Us Empty in the Soul35:14 — The Cult of Trauma and the Victim Mindset43:00 — Three Pillars to Design Friction in Your Life48:52 — The 747 Club Invitation: Book the Flight, I Dare You👋It’s your host, Brian! Come say hi!Website: https://brianondrako.comLinkedIn: https://www.linkedin.com/in/brianondrako/ Or, if you’re struggling with sales, join the Sales Skills For Founders newsletter and learn how to lead better sales conversations, spot weak deals early, and build a pipeline you can actually trust.📨 https://salesskillsforfounders.com

Teresa Quinlan is an executive leadership coach and accomplished athlete who specializes in the intersection of emotional intelligence and leadership excellence. She works with CEOs, SVPs, and mid-level leaders who are willing to do the real work of developing their EQ — not just their technical skills.In this episode, Teresa breaks down the difference between emotional intelligence (EI) and the emotion quotient (EQ), and introduces her powerful framework: IQ + EQ = TQ (Talent Quotient). You'll discover why most people's view of emotional intelligence is far too narrow, which two overlooked EQ skills — independence and flexibility — are holding leaders back, and how to use the ABCDE method to build emotional self-awareness starting today. Whether you're leading a team, raising a teenager, or just trying to show up better in your own life, this conversation delivers practical, immediately actionable insight.Chapters:0:00 — Welcome & Intro to Teresa3:36 — Who Teresa Works With8:10 — EI vs. EQ: Clearing Up the Confusion12:42 — The IQ + EQ = TQ Equation16:19 — Rapid Fire Question 1: Momentum Over Motivation18:15 — Rapid Fire Question 2: Redefining Enough22:09 — Rapid Fire Question 3: Who Teresa Admires for Taking Action25:44 — Rapid Fire Question 4: Teresa's High-Touch Operating System28:09 — Rapid Fire Question 5: How Teresa Approaches Goal Setting30:33 — How to Know When You Need to Work on Your EQ34:20 — When Excitement Becomes an EQ Problem38:13 — The 15 EQ Skills (And Why Most People Only Know 2)40:41 — The Overlooked Skill: Independence42:39 — The Overlooked Skill: Flexibility45:58 — A Real-Time EQ Practice for Parents and Leaders51:27 — One Action to Start Building Better EQ Today (The ABCDE Method)Find Teresa Online:Website: https://www.iqeqtq.comLinkedIn: https://www.linkedin.com/in/teresaquinlan12/Instagram: https://www.instagram.com/teresaquinlan12/YouTube: https://www.youtube.com/@teresaquinlan6292👋It’s your host, Brian! Come say hi!Website: https://brianondrako.comLinkedIn: https://www.linkedin.com/in/brianondrako/ Or, if you’re struggling with sales, join the Sales Skills For Founders newsletter and learn how to lead better sales conversations, spot weak deals early, and build a pipeline you can actually trust.📨 https://salesskillsforfounders.com

Casey Brown, pricing expert and author of Fearless Pricing, shares her journey from chemical engineer to entrepreneur and pricing consultant. Casey unpacks why most businesses — regardless of size or industry — are leaving money on the table due to fear-based pricing decisions. She explains the psychology behind underpricing, the dangers of unnecessary discounting, and why a customer objecting on price is actually a buying signal. Casey also gets personal about her path from poverty to Fortune 500 to founder, the lessons of niching down early, the importance of meditation, and her evolving pursuit of a more intentional, peaceful pace of work.Chapters:00:00 Intro & Elevator Pitch03:10 The Origin of a Pricing Geek05:20 The Leap from Corporate to Entrepreneur10:10 Niche Down Sooner13:55 Post-It Note Wisdom17:50 Mantra & Mindset Under Pressure19:30 Imposter Syndrome & Self-Doubt26:55 Pricing Blind Spots & Fears30:55 How to Set the Right Price42:20 Price Objections Are Buying Signals44:50 Why You Need Pricing Meetings47:40 Action Item & Fearless PricingFind Casey Online:Personal Website: www.caseybrown.comBusiness Website: www.boostpricing.comLinkedin: www.linkedin.com/in/caseybrownboost/Youtube: www.youtube.com/@boostpricing👋It’s your host, Brian! Come say hi!Website: https://brianondrako.comLinkedIn: https://www.linkedin.com/in/brianondrako/ Or, if you’re struggling with sales, join the Sales Skills For Founders newsletter and learn how to lead better sales conversations, spot weak deals early, and build a pipeline you can actually trust.📨 https://salesskillsforfounders.com

Tyler Denk built beehiiv after seeing how chaotic newsletter ops were at Morning Brew—writers pasting Google Docs into fragile HTML, ads tracked in spreadsheets, growth tools scattered everywhere. beehiiv’s goal: one ecosystem for publishing, growth loops, monetization, websites, surveys, and automations. Tyler explains the double-edged sword of shipping fast: it wins users, but every feature creates maintenance debt, and one weak feature can taint the whole product. He shares what newsletter formats win, why owned distribution matters for companies, and how he monetizes beyond ads through high-ticket founder masterminds.Chapters:0:00 Welcome + Tyler’s newsletter journey0:40 The Morning Brew problem: “duct-taped” systems everywhere3:04 Building the referral program + growth mechanics3:35 Leaving Morning Brew: non-compete tension and rebuilding trust4:42 beehiiv’s vision: growth + monetization + platform ecosystem6:07 Product philosophy: shipping fast vs. maintaining quality12:01 Fixing surveys + the “cool down week” operating rhythm15:19 What newsletter formats win right now?17:06 Big Desk Energy origin story17:49 If Tyler had to start over: what newsletter he’d build now20:36 Costa Rica masterminds + monetizing beyond sponsorships20:49 Rapid Fire Q1: Book that shaped him most22:35 Rapid Fire Q2: How he filters advice23:41 Rapid Fire Q3: Fear he hasn’t shaken27:45 Rapid Fire Q4: Reset button for stress31:09 Rapid Fire Q5: Fortune cookie message + “only control effort”36:57 Newsletter checklist for companies: why owned distribution matters41:27 Action item: test internally, iterate, then publish43:31 Wrap-up + where to find TylerBeehiiv: https://www.beehiiv.com Linkedin: https://www.linkedin.com/in/tyler-denk/ Twitter: https://x.com/denk_tweets Big Desk Energy Newsletter: https://mail.bigdeskenergy.com/ 👋It’s your host, Brian! Come say hi!Website: https://brianondrako.comLinkedIn: https://www.linkedin.com/in/brianondrako/ Or, if you’re struggling with sales, join the Sales Skills For Founders newsletter and learn how to lead better sales conversations, spot weak deals early, and build a pipeline you can actually trust.📨 https://salesskillsforfounders.com