Deal With It: How I Failed This

Igor Vainshtein
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  • Entrepreneurship

Deal With It: How I Failed This is a podcast about the failures behind the success stories. Hosted by bestselling author, speaker, and serial entrepreneur Igor Vainshtein, each episode features candid conversations with founders, entrepreneurs, and high performers about the moments that didn’t go according to plan: failed businesses, bad decisions, missed opportunities, painful pivots, and the lessons that came from them. Because success rarely happens in a straight line. Igor and his guests unpack what went wrong, how they dealt with it, and how those experiences ultimately shaped the businesses, careers, and lives they have today. No polished highlight reels. No pretending everything worked the first time. Just honest stories about failure, resilience, reinvention, and figuring out what comes next. You failed. You learned. You dealt with it.

Episodes

  1. 2d ago

    Ep. 8 Why Taking the Wrong Investment Was This Founder’s Biggest Screw-Up - Alan Shields

    Episode Description What if the investment you wanted wasn’t the investment you needed? In this episode of Deal With It: How I Failed This, Igor Vainshtein sits down with Alan Shields, co-founder of RFI Global, to unpack the highs and lows of building a global data and insights business from two bedrooms in Sydney. Alan explains why taking a high valuation from a hands-off investor at the wrong stage became his biggest screw-up, and why what the business needed was experience, guidance and networks, not just a cheque. From the 2008 financial crisis hitting a young startup to the challenge of cracking the US market, Alan shares the non-linear path from two founders to a global team of 100+, and the 2020 private equity deal that finally delivered the kind of investor he’d been looking for. He also makes the case for hiring on curiosity over a polished CV. It’s a masterclass for any entrepreneur weighing control against the outside push needed to go global. What You’ll Learn Why “smart money” can matter more than a high valuationWhy the type and timing of investment matter more than the investorHow the 2008 financial crisis hit a young startup, and how a low-cost, subscription-based model helpedWhy hiring for curiosity beats hiring for brand-name CVsThe reality of “work-life balance” in the first decade of bootstrappingWhy the US market is so hard to crack, and the workarounds RFI found (niche segments, an acquisition, and Canada)About the Guest Alan Shields is a co-founder of RFI Global, a leading data and insights firm for the financial services sector. Since 2006, he helped grow the business from two founders to a global team of 100+ across Sydney, London, Singapore and North America, including a 2020 investment from Los Angeles-based Diversis Capital. Alan is an expert in turning complex data into compelling stories and is the author of The Startup Handbook: A Founder’s Guide to Building a Business. He now serves on the RFI board and mentors startups on fundraising and market strategy. About the Host Igor Vainshtein is a serial entrepreneur and author of Practical Manifestation and Agile Manifestation. As the founder of GolfTrak, and previously of 24-7 Golf (acquired by GOLFTEC), he has experienced the full spectrum of the founder’s journey, from exits to significant setbacks. On Deal With It: How I Failed This, Igor strips away the entrepreneurial highlight reel to explore failure as a tool for growth and the practical lessons that come from life in the arena. Books, Quotes and Concepts Mentioned The Startup Handbook: A Founder’s Guide to Building a Business by Alan ShieldsPractical Manifestation and Agile Manifestation by Igor VainshteinOscar Wilde: “Experience is just the name we give our mistakes”The “hacker and hunter” co-founder dynamicOutcome-based hiring vs. functional job descriptionsDaniel Priestley’s “plumbers will out-earn lawyers” comment on The Diary of a CEOFollow and Connect Alan Shields LinkedIn: https://www.linkedin.com/in/abjshields/ Igor Vainshtein LinkedIn: https://www.linkedin.com/in/igorvainshtein/ Website: https://igorvainshtein.com/ Podcast: https://igorvainshtein.com/how-i-failed-this-podcast

  2. Oct 23

    Ep. 7 How Snowball Moments Shape Success - Yuan Wang

    Episode Description What if working harder is actually making things worse? In this episode, Igor Vainshtein sits down with entrepreneur Yuan Wang to unpack the moment everything started to crack, despite doing all the "right" things. After years of grinding, running two businesses, and chasing success, Yuan reached a breaking point: burnout, financial pressure, strained relationships, and the brutal realization that one of his companies had no real value after five years of work. From a wake-up call in the back of an Uber to a complete shift in mindset, this conversation explores the truth about self-doubt, identity, and what it really takes to turn things around. If you have ever thought, "I'll feel better when I succeed," this episode will challenge that belief. What You Will Learn * Why working harder does not fix self-doubt * The hidden cost of being constantly busy * How failure builds real confidence * When pain becomes the trigger for change * Why entrepreneurs should not build alone * The mindset shifts that changed everything About the Guest Yuan Wang is a UX designer turned entrepreneur. After leaving advertising in 2013, he founded Yump, a digital agency that serves nonprofits, and co-founded Studio Ninja, workflow software for photographers that grew to customers in Australia, New Zealand, the UK, and the US. Both businesses were bootstrapped without outside investors, and both were later sold. Yuan is currently writing Customers, Not Investors, a book about building a company without external funding. About the Host Igor Vainshtein is a serial entrepreneur and best-selling author of Practical Manifestation and Agile Manifestation. As the founder of GolfTrak, he has navigated the full spectrum of the founder's journey, from high-stakes exits to significant business setbacks. On his podcast, How I Failed This, Igor strips away the entrepreneurial highlight reel to explore failure as a vital tool for growth. He focuses on building resilient leadership and uncovering the raw, practical lessons that only come from navigating life in the arena. Books and Resources Mentioned * Key Person of Influence (program) by Daniel Priestley * Buy Back Your Time by Dan Martell * The E-Myth by Michael Gerber * Antifragile by Nassim Nicholas Taleb * Entrepreneurpoly board game: https://www.entrepreneurpoly.net * Customers, Not Investors by Yuan Wang (Work in Progress): https://customersnotinvestors.com Follow and Connect Yuan Wang LinkedIn: https://www.linkedin.com/in/yuan-wang-b2618640/ Websites: https://www.yump.com.au and https://www.studioninja.co Igor Vainshtein LinkedIn: https://www.linkedin.com/in/igorvainshtein/ Website: https://igorvainshtein.com/ Podcast: https://igorvainshtein.com/how-i-failed-this-podcast

  3. Oct 16

    Ep. 6 Clarity in the Chaos: Using the Three C's to Navigate Business Failure - Slayman Abou Hamdan

    Episode Description In this episode of How I Failed This, Igor Vainshtein sits down with Sleiman “Slayman” Abou-Hamdan, a psychologist, executive coach, and leadership strategist who played a critical role in helping Igor navigate his own journey through failure. Slayman shares his path to success—from serving as a platoon commander in the Australian Army Infantry to navigating a paralyzing career setback in a senior government leadership meeting. Slayman explains why human connection and Emotional Intelligence are the true differentiators as AI continues to evolve. He breaks down his 3Cs Model™ (Clarity, Courage, Connection) and reveals a powerful perspective shift: why our biggest failures and reactive moments are often just "strengths over-indexed," and how to break free from the addictive cycle of self-criticism. What You’ll Learn Why your biggest failures and reactive moments are actually your greatest strengths functioning in overdrive.Why Emotional Intelligence (EI) and connected human ideation are your best advantages against AI.How to master the 3Cs Model™: Clarity, Courage, and Connection.High-stakes leadership lessons from military infantry applied to the boardroom.How to keep moving forward and turn "stale water" into "running water" by taking the immediate first step.The importance of surrounding yourself with a Coach, Confidant, Critic, and Cheerleader.About the Guest Sleiman "Slayman" Abou-Hamdan is a psychologist, executive coach, leadership strategist, former Australian Army Infantry Officer, and the founder of Holistic Psychology Australia. Specializing in high-performance leadership, he works with entrepreneurs, elite athletes, and high-stakes professionals to build resilience and emotional intelligence. He is the author of Emotional Intelligence in the Age of AI. About the Host Igor Vainshtein is a serial entrepreneur and best-selling author of Practical Manifestation and Agile Manifestation. As the founder of GolfTrak, he has navigated the full spectrum of the founder’s journey, from high-stakes exits to significant business setbacks. On his podcast, How I Failed This, Igor strips away the entrepreneurial highlight reel to explore failure as a vital tool for growth. He focuses on building resilient leadership and uncovering the raw, practical lessons that only come from navigating life in the arena. Books and Concepts Mentioned Practical Manifestation by Igor VainshteinAgile Manifestation by Igor VainshteinEI for the Age of AI by Sleiman Abou-HamdanThe 3Cs Model™ – Clarity, Courage, and ConnectionZone Management – Moving from reactivity to regulationThe FDC Framework – Understanding behavioral reactivitiesFollow and Connect Mr. Slayman LinkedIn: https://www.linkedin.com/in/slaymanabouhamdan/ Websites:https://slayman.com.au/ and holisticpsychology.com.au Igor Vainshtein LinkedIn: https://www.linkedin.com/in/igorvainshtein/ Website: https://igorvainshtein.com/

  4. Oct 9

    Ep. 5 Resilience in Golf and Life - Nadene Gole

    Episode Description What if walking away from the game is exactly what brings you back stronger? In this episode, Igor Vainshtein sits down with Nadine Gole, a former world No. 1 senior amateur golfer, to explore a journey that challenges the traditional path of success in sport. From early competitive golf to stepping away from the game entirely, Nadine shares how burnout, pressure, and shifting priorities shaped her career. After years away, she returned to golf with a completely different mindset, one focused less on outcomes and more on process, discipline, and enjoyment. That shift ultimately led her to become the No.1 ranked senior amateur golfer in the world. This episode is a powerful look at longevity, reinvention, and how stepping back can sometimes be the move that changes everything. What You’ll Learn Why stepping away can lead to better long-term performanceThe impact of burnout and pressure in competitive environmentsHow mindset shifts can transform resultsWhy process matters more than outcomesHow to sustain performance over a long period of timeThe role of discipline and perspective in high-level competitionAbout the Guest Nadine Gole is an Australian golfer and former world No. 1 ranked senior amateur. After stepping away from competitive golf for several years, she returned to the sport and reached the top of the global rankings through a renewed focus on mindset, consistency, and long-term development. Her journey reflects a non-linear path to success, shaped by resilience, perspective, and a deep understanding of performance over time. About the Host Igor Vainshtein is a serial entrepreneur and best-selling author of Practical Manifestation and Agile Manifestation. As the founder of GolfTrak, he has navigated the full spectrum of the founder’s journey, from high-stakes exits to significant business setbacks.  On his podcast, How I Failed This, Igor strips away the entrepreneurial highlight reel to explore failure as a vital tool for growth. He focuses on building resilient leadership and uncovering the raw, practical lessons that only come from navigating life in the arena. Books and Concepts Mentioned Process-driven performance vs outcome-based thinkingManaging burnout and long-term sustainabilityMindset shifts in competitive environmentsFollow and Connect Nadine Gole Instagram: https://www.instagram.com/nadenegole/ Igor Vainshtein LinkedIn: https://www.linkedin.com/in/igorvainshtein/ Website: https://igorvainshtein.com/

  5. Oct 2

    Ep. 4 The Power of Resilience and Clarity in Business - Leah Akoka

    Episode Description What happens when blind ambition and the "just do it" mentality crash into reality? In this episode, Igor Vainshtein sits down with Leah Akoka, founder of Wall Street and creator of the People Economics framework, to explore her journey from managing the people side of Dodo Internet to redefining the modern workplace. Leah shares the raw story of rapidly opening five retail stores in under six months, the arrogance that drove the project, and the inevitable failure that followed. She reveals how this massive setback taught her the critical difference between mere activity and strategic patience. The conversation dives deep into why traditional HR is fundamentally flawed and how focusing on outcomes rather than tasks can turn employees into true ambassadors for your business. This episode offers a practical perspective on decision-making, ego, and the million little things that actually create sustainable success. What You’ll Learn Why rapid iteration and blind activity can sabotage progress if you lack strategic patience.The hidden costs of taking a "cookie-cutter" approach when expanding into different business models.How to rewrite job descriptions by focusing purely on outcomes rather than a checklist of tasks.Why truly effective Human Resources actually means having no traditional HR department.The crucial difference between losing a single battle and losing the entire war in business.How to structure leadership to help every employee believe they are capable of greatness.About the Guest Leah Akoka is the founder of Wall Street and creator of the People Economics framework, a model designed to drive performance through alignment, outcomes, and culture. Drawing from her foundational experience managing the people side of Dodo Internet—helping scale the company from 3 to over 500 employees—she now helps businesses build accountable, high-performing teams. Her leadership approach heavily integrates principles of Neuro-Linguistic Programming (NLP) and behavioral economics. About the Host Igor Vainshtein is a serial entrepreneur and best-selling author of Practical Manifestation and Agile Manifestation. As the founder of GolfTrak, he has navigated the full spectrum of the founder’s journey, from high-stakes exits to significant business setbacks. On his podcast, How I Failed This, Igor strips away the entrepreneurial highlight reel to explore failure as a vital tool for growth. Books and Concepts Mentioned Neuro-Linguistic Programming (NLP) foundations in people management.Agile methodology and defining "acceptance criteria" for success.Simon Sinek’s Start With Why.The "million little things" philosophy of success and relationship building.Follow and Connect Leah Akoka LinkedIn: https://www.linkedin.com/in/leahakoka/Website: https://wallst.com.au/people-economics/Igor Vainshtein LinkedIn: https://www.linkedin.com/in/igorvainshtein/Website: https://igorvainshtein.com/

  6. Sep 25

    Ep. 3 The Hidden Lessons in Failure - Armin Sadeghi

    Episode Description From building products at Microsoft to leading companies as a founder, Armin Sadeghi has seen success from the inside. But his biggest insight challenges the way most people think about failure. In this episode, Igor Vainshtein sits down with Armin Sadeghi to break down why failure is not something to avoid, but a necessary part of growth. Drawing from his early business ventures after leaving Microsoft, Armin shares how moving too slowly to build a prototype and failing to get rapid customer feedback became the foundation for his long-term success. The conversation explores how society defines success, why most people never question it, and how redefining your own criteria, or "acceptance criteria", can change how you operate in both business and life. This episode offers a practical framework for thinking about failure, decision-making, and building momentum through action. What You’ll Learn Why failure is not an endpoint but a continuous learning process.The severe cost of moving too slowly and ignoring rapid customer feedback loops.Why you shouldn't bootstrap a capital-intensive business or try to solve massive market problems as a side hustle.How reading biographies can serve as a powerful tool to learn from the failures of others.How redefining success as a daily practice changes your decisions and priorities. About the Guest Armin Sadeghi is a technology leader and entrepreneur with over two decades of experience building and scaling products. He previously worked at Microsoft, where he contributed to globally scaled products, and has since held executive roles, including CTO and General Manager, across multiple industries. He focuses on best-practice product development, strategic planning, and solving genuine business problems. About the Host Igor Vainshtein is a serial entrepreneur, founder of GolfTrak, and best-selling author of Practical Manifestation and The Agile Manifestation. On his podcast, How I Failed This, Igor strips away the entrepreneurial highlight reel to explore failure as a vital tool for growth, focusing on building resilient leadership and uncovering the raw, practical lessons that only come from navigating life in the arena. Books and Concepts Mentioned Biographies as a tool for learning from others’ failures.Agile methodology and iterative development.Feedback loops and rapid validation in product building.Success as a self-defined "acceptance criteria" rather than a societal metric. Follow and Connect Armin Sadeghi: LinkedIn | WebsiteIgor Vainshtein: LinkedIn | Website

  7. Sep 11

    Ep. 2 How Goalkeeping Teaches Leadership and Resilience - Bernie Fernandez

    Episode Description In this episode of How I Failed This, Igor Vainshtein and Agero Group Founder Bernie Fernandez explore the psychology of the Goalkeeper Mindset. Reflecting on his years as a soccer goalkeeper, where every mistake was amplified, Bernie explains how that unique accountability shaped his leadership style in the commercial construction industry. Bernie further dives into the dangers of society's "cotton wool" culture, the necessity of high-stakes environments for growth, and how he uses AI to stabilize core business operations so he can focus on authentic human connection. What You’ll Learn Why the goalkeeper’s position is the ultimate training ground for business accountability.The danger of participation certificates and the need for high-stakes environments in personal growth.How to move from a destruction-based definition of failure to a daily practice mindset.Using the bamboo proverb to stabilize your business base before seeking exponential growth.Why AI is a tool for operational stability that frees humans to lead with authenticity. About the Guest Bernie Fernandez is an entrepreneur and the Founder of Agero Group, a firm specializing in commercial property and office fit-outs. A former goalkeeper, he translates the discipline of competitive sport into a leadership philosophy centered on resilience, operational stability, and the belief that building a safe home base is the prerequisite for any successful venture. About the Host Igor Vainshtein is a serial entrepreneur, founder of GolfTrak, and best-selling author of Practical Manifestation and The Agile Manifestation. On his podcast, How I Failed This, Igor strips away the entrepreneurial highlight reel to explore failure as a vital tool for growth, focusing on building resilient leadership and uncovering the raw, practical lessons that only come from navigating life in the arena. Books and Concepts Mentioned The Agile Manifestation by Igor VainshteinAntifragile by Nassim TalebThe Bamboo Principle: Focusing on a stable base before rapid growth.The Goalkeeper Mindset: Carrying the failure of the team to build accountability. Follow and Connect Bernie Fernandez: LinkedInIgor Vainshtein: LinkedIn | Website

  8. Sep 3

    Ep. 1 How Elite Performers Use Failure to Get Better - Mark Dobson

    Episode Description What if the difference between a gold medal and a failure was just one-hundredth of a second? In this episode of How I Failed This, Igor Vainshtein sits down with Mark Dobson, an Australian performance advisor and speaker, to uncover the mindset shifts that drive elite athletes and CEOs to the top. Mark shares his early career heartbreak, bombing at a local stand-up comedy talent show, and how that brutal failure taught him the non-negotiable formula for winning audience rapport. From pioneering a livestream setup during his child's birth to avoid missing a corporate roadshow, to coaching Olympic swimmers like Grant Hackett and Marika Gura through the margins of success, Mark explores the true definition of failure. This conversation is a masterclass for leaders and high-achievers looking to move beyond average, navigate uncertainty, and define what authentic success looks like outside of the boardroom. What You’ll Learn Why bombing on stage teaches you the importance of getting three quick "yeses" from your audience.The difference between procrastination and deliberately "holding the uncertainty" to relieve stress by setting a decision date.Why elite athletes clearly define failure, whereas most businesses only set targets without defining what failure actually means.How to manage the unique vulnerabilities, lifestyle imbalances, and blind spots of hyper-talented "freak performers" like coders and Olympic athletes.The importance of maintaining a "reverence for the task at hand" and avoiding cockiness, no matter your level of experience.How to separate your core self-esteem from the outcomes of your professional failures. About the Guest & Host Mark Dobson: A performance expert and keynote speaker who helps individuals and teams achieve elite results. He advises world champions to achieve personal bests and applies high-performance sports principles to guide corporate leaders. Author of Rise Above and No Wasted Effort.Igor Vainshtein: Serial entrepreneur, founder of GolfTrak, and best-selling author of Practical Manifestation and The Agile Manifestation. He explores failure as a vital tool for growth and building resilient leadership. Books and Concepts Mentioned No Wasted Effort by Mark Dobson.The Trick to Money Is Having Some by Stuart Wilde.The Agile Manifestation by Igor Vainshtein.Tony Robbins' Concept: "How we do one thing, we do everything".The "Three Yeses" formula for building immediate audience rapport.Janine Allis and Jeff Harris' Handshake Investment Story. Follow and Connect Mark Dobson: LinkedIn | WebsiteIgor Vainshtein: LinkedIn | Website

  • 8 Episodes

About

Deal With It: How I Failed This is a podcast about the failures behind the success stories. Hosted by bestselling author, speaker, and serial entrepreneur Igor Vainshtein, each episode features candid conversations with founders, entrepreneurs, and high performers about the moments that didn’t go according to plan: failed businesses, bad decisions, missed opportunities, painful pivots, and the lessons that came from them. Because success rarely happens in a straight line. Igor and his guests unpack what went wrong, how they dealt with it, and how those experiences ultimately shaped the businesses, careers, and lives they have today. No polished highlight reels. No pretending everything worked the first time. Just honest stories about failure, resilience, reinvention, and figuring out what comes next. You failed. You learned. You dealt with it.

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