the Learn-It-All™ podcast

What happens when you’re good enough to get in the room — and then don’t like what you see?CJ Davidson spent years grinding his way up in traditional financial services. Cold-calling attorneys from a $5 street tie. Earning trust one client at a time. Building something real.And then, when he finally got a seat in the leadership meetings, he realized the client wasn’t even in the conversation.That moment didn’t break him. It built Proxy Financial.In this episode of The Learn-It-All Podcast, Damon sits down with CJ — Founder and CEO of Proxy Financial — to talk about what it actually takes to build a culture where doing the right thing when no one is looking isn’t a policy. It’s the whole point.This one goes well beyond financial advice. It’s about curiosity over compliance, art over script, and what happens when you stop asking permission to do things that just make sense.In This Episode, You’ll LearnWhy CJ got pushback for buying his clients cocktails — and how that moment revealed everything wrong with the system he was inThe difference between a financial professional who’s technically sharp and one who’s actually right for youWhy you don’t need a lot of money to benefit from a great advisor — you need a goal you’re not confident executing aloneHow CJ thinks about AI: not as a threat, but as the thing that finally frees advisors to do the human work that actually builds trustWhy he tells aspiring financial professionals to major in psychology and minor in financeWhat “doing the right thing when no one is looking” looks like inside a company built around itChapters00:00 Episode preview and introduction00:54 What CJ Davidson saw inside traditional financial services03:48 The “art and science” of financial advice05:14 The client mixer idea that challenged the old playbook09:27 Moving from advisor to leadership and teaching fiduciary thinking11:41 Seeing how “the soup was made” inside corporate finance14:33 Why CJ helped build Proxy Financial16:22 How to test a business hypothesis before going all in17:50 Building a mission-aligned culture on a distributed team19:03 How to choose a financial advisor who is actually the right fit25:26 Proxy Financial’s long-term vision and advisor succession28:06 Ethics, temptation, and doing the right thing when no one is looking30:25 How AI is changing financial advice without replacing human trust33:45 Where listeners can connect with CJ Davidson35:33 CJ’s take on confidence vs. arroganceAbout CJ DavidsonCJ Davidson is the Founder and CEO of Proxy Financial. He works closely with financial advisors and business owners who want to do right by their clients while building businesses designed to last. His approach is centered on ethical, relationship-first financial advice, long-term protection, and sustainable growth. CJ also takes a holistic view of wealth that includes health, perspective, and balance.Resources and MentionsCJ Davidson’s LinkedIn: https://www.linkedin.com/in/cjdavidsonplanner/Proxy Financial’s website: https://www.proxyfinancial.com/Marked Unread Podcast: https://www.proxyfinancial.com/marked-unread-podcast/Working Genius: https://www.tablegroup.com/workinggenius/Unreasonable Hospitality book: https://www.amazon.com/Unreasonable-Hospitality-Remarkable-Giving-People/dp/0593418573Podcast Contact Information:Website: www.learnit.comEmail: [email protected] us on LinkedIn and Instagram for updates.

What if the promotion you want is the very thing that could derail your career?In this episode of The Learn-It-All™ Podcast, Damon Lembi sits down with Vincent Wanga, award-winning creative executive and author of The Art of Direction, to unpack the first question every high performer should ask before becoming a leader: why? Vincent explains why leadership is not just the next step for top individual contributors, why chasing money, power, and glory is a dangerous reason to say yes, and why leading people is ultimately an empathetic and selfless pursuit. He also breaks down the difference between execution skills and leadership skills, why some of the best performers fail once they move into management, and how to know whether leadership is actually aligned with who you are.Drawing from his own improbable career, from getting kicked out of art school to freelancing his way back into the industry, scaling teams in high-growth tech, and learning hard lessons through failure, Vincent shares practical leadership advice for emerging leaders, entrepreneurs, executives, and ambitious professionals navigating career growth in an AI-driven world.Damon and Vincent also explore delusional optimism, accountability, confidence versus arrogance, corporate politics, mentorship, and the human skills that matter most in modern leadership, including empathy, decisiveness, adaptability, and relationship-building. If you are wondering whether leadership is the right path for you, or how to become a stronger leader without losing yourself in the process, this conversation is packed with real-world insight.In This Episode, You’ll Learn:Why the first question to ask before accepting a leadership role is not about salary, title, or power, but why you want it in the first placeHow great executors get pushed into leadership roles that do not fit them, and what to do if you already took the job and know it was the wrong moveThe difference between confidence and arrogance, and why Vincent says failure taught him more than books, podcasts, and “pocket MBAs” ever didWhy empathy, politics, decisiveness, and relationship-building are still the real human advantage in an AI worldWhy mentorship is everything, and why real leaders should see developing people as part of their legacyTimestamps00:00 Episode preview00:42 The first question to ask before saying yes to leadership02:29 Why leadership is not for everybody04:59 What to do if you have already accepted the wrong leadership role08:04 Vincent Wanga’s improbable path into creativity and leadership10:02 Getting kicked out of school and rebuilding from scratch12:24 What to do after losing your dream job15:31 Delusional optimism, entrepreneurship, and betting on yourself19:06 The branding project that humbled Vincent’s ego25:17 Scaling a team 20x and the leadership lesson that stayed with him31:03 Why Vincent wrote The Art of Direction35:36 Gen Z, alternate paths, and redefining leadership37:16 The human skills that matter most in the AI era42:08 How leaders should handle executive pushback and boardroom politics47:24 AI as a tool, not a crutch53:13 Why mentorship is everything58:24 What leadership could look like 20 years from now01:01:22 Where to connect with Vincent WangaAbout Vincent WangaVincent Wanga is a creative leader, entrepreneur, and author of The Art of Direction: Personal Perspectives on the Path to Creative Leadership. Originally from Kenya and raised in the Twin Cities, Vincent built a two-decade career across design, branding, entrepreneurship, agency leadership, and high-growth tech. His journey has included early setbacks, major reinvention, executive leadership, and hard-earned lessons around accountability, resilience, empathy, and business outcomes.Resources and MentionsThe Art of Direction: Personal Perspectives on the Path to Creative Leadership: https://www.amazon.com/Art-Direction-Personal-Perspectives-Leadership/dp/B0DXJ4MLG7Vincent Wanga’s website: ​​https://www.vincentwanga.com/Vincent Wanga’s LinkedIn: https://www.linkedin.com/in/vincent-wanga/Good to Great book by Jim Collins: https://www.amazon.com/Good-Great-Some-Companies-Others/dp/0066620996The 7 Habits of Highly Effective People by Stephen R. Covey: https://www.amazon.com/Habits-Highly-Effective-People-Powerful/dp/0743269519Podcast Contact Information:Website: www.learnit.comEmail: [email protected] us on LinkedIn and Instagram for updates.

What does it really take to walk into a company everyone says is finished and turn it into a comeback story?In this episode of The Learn-It-All™ Podcast, Damon Lembi sits down with legendary operator and investor Ray Lane for a masterclass on leadership, company turnarounds, founder potential, and scaling a business without losing the plot. Ray shares the hard-earned lessons that took him from an unexpected first leadership role in college to IBM, EDS under Ross Perot, the high-stakes turnaround of Oracle, Kleiner Perkins, and now GreatPoint Ventures.This conversation goes deep into how to turn around a struggling company, what great founders do differently, why most technical founders make the same go-to-market mistake, and how leaders build organizations that can actually scale. Ray breaks down what Oracle looked like when he arrived, why the company had become a “wild wild west,” how he rebuilt customer trust, and why leadership is not just about winning battles but winning the war. He also explains the critical difference between a founder, an entrepreneur, and a CEO, what he looks for in startup pitches today, and why the first 30 seconds of a founder’s explanation can tell you almost everything.If you are a founder, executive, operator, investor, or aspiring leader trying to understand startup leadership, software company scaling, sales organization transformation, venture capital founder advice, or how great leaders inspire performance, this episode is packed with practical insight and real-world stories from the front lines of Silicon Valley.In This Episode, You’ll Learn:Why Ray Lane says people leave for context and get recruited away for content, and what that means for retaining top performersWhat IBM taught him about discipline, structure, and leadership development, and what EDS taught him that IBM never couldWhy Ross Perot’s interview style forced Ray to stop hiding behind company credentials and explain why he was the right personWhat Oracle looked like when Ray joined, why customers had lost confidence, and how bad the mess really was behind the scenesHow Ray rewrote Oracle’s sales rules, ripped up bad customer contracts, and moved the company away from short-term wins that destroyed long-term trustThe difference between a diminisher and a multiplier, and why Ray believes leaders should inspire people, not shrink themWhy most founders are not automatically entrepreneurs, and most entrepreneurs are not automatically CEOsWhat Ray looks for in a startup pitch, including why a founder should be able to explain the problem and opportunity in 30 secondsTimestamps[00:00] Episode preview and introduction[02:29] Ray’s first leadership role and the surprise of becoming fraternity president[04:21] Setting a bold goal and scaling the fraternity from 25 to 125 brothers[06:54] How college leadership built Ray’s confidence and social fluency[09:11] IBM’s culture, structure, and the belief that anyone could become CEO[10:38] The call that pulled Ray from IBM to EDS[11:48] Ross Perot’s intense interview and why Ray wanted in[13:01] What EDS taught Ray about hiring, P&L ownership, and pressure[15:26] Trial and error leadership versus the IBM playbook[19:28] Facing risk, buying software, and learning to take responsibility[22:08] Why Ray left EDS and the leadership lesson behind it[24:19] Booz Allen, rapid growth, and the CEO path Ray thought he wanted[25:21] The recruiter call about Oracle and why it did not look attractive[29:11] Ray’s four-hour meeting with Larry Ellison[31:16] Oracle’s broken model and the vision that changed Ray’s mind[35:13] Rewriting Oracle’s rules and rebuilding the business[36:58] Why Oracle was worse than Ray expected when he got inside[40:35] The data that shocked Ray most: customers disliked Oracle[42:30] Killing Sybase and building Oracle’s applications and consulting engine[51:22] Multipliers vs diminishers and Ray’s leadership philosophy[54:28] Winning battles versus winning the war[59:05] Why Oracle taught Ray more than IBM or EDS ever did[01:01:05] “Be a leader, inspire people,” and the difference between managers and leaders[01:04:10] What Ray Lane looks for in founders today[01:06:41] Why most founders get go-to-market wrong[01:09:29] From Oracle to Kleiner Perkins to GreatPoint Ventures[01:13:37] The kind of AI and healthcare founder Ray wants to backAbout Ray LaneRay Lane is a veteran technology executive, operator, and investor best known for helping lead one of the most important turnarounds in enterprise software history at Oracle, where he served as President and COO. Before Oracle, he built his leadership foundation at IBM, sharpened his operator instincts under Ross Perot at EDS, and later became a senior leader at Booz Allen Hamilton. After Oracle, Ray spent 14 years as a Managing Partner at Kleiner Perkins, working closely with founders and high-growth companies, and he is now the Co-Founder and Managing Partner of GreatPoint Ventures, where he focuses on backi

What if the very thing parents try hardest to protect their kids from is exactly what helps them grow?In this solo episode of The Learn-It-All™ Podcast, Damon Lembi shares why Little League baseball teaches kids to fail, and why that’s one of the greatest gifts youth sports can offer. From the excitement of opening day and breaking in a new glove with his dad, to striking out four times in one game at Arizona State, Damon reflects on the life and leadership lessons that started on the baseball field.This episode is a powerful reminder for parents, coaches, and leaders that youth sports are about far more than wins and losses. They teach kids how to show up, compete, be a good teammate, handle disappointment, and build resilience through failure. Damon also challenges parents not to “bubble wrap” their kids or make excuses when things do not go their way. Instead, he makes the case for letting failure become a learning moment that builds courage, confidence, and character.If you care about raising resilient kids, coaching with intention, teaching confidence through sports, or helping young athletes handle failure, this episode is packed with practical perspective and hard-earned wisdom from Damon’s own journey in Little League, college baseball, leadership, and life.In This Episode, You’ll Learn:What Damon believes parents and coaches get wrong when they make excuses instead of helping kids grow through setbacksThe story of not making a youth soccer team and the tough-love lesson Damon’s dad gave him that stayed with him foreverHow Damon rebounded after striking out four times in one game at Arizona State, and what his coach said that restored his confidenceWhy Little League is not really about winning or losing, but about showing up, giving your best, being a good teammate, and having funHow youth sports help kids develop the confidence, discipline, and courage they’ll later need in leadership, business, and lifeTimestamps00:00 – Opening memories of Little League and the joy of getting ready for the season01:15 – Damon’s salute to parents and coaches who make youth sports possible01:47 – The lifelong skills kids learn through sports, from teamwork to discipline02:09 – Why parents and coaches need to let kids fail instead of bubble wrapping them02:28 – Damon’s story of not making the soccer team and the lesson his dad taught him03:18 – Striking out four times against Michigan and what happened the next day04:21 – Why sports gave Damon the courage to lead teams and work with thousands of leaders04:43 – What Little League is really about, and why winning is not the point05:38 – Damon’s message to parents about support, perspective, and having a great season06:00 – Closing thoughts and who this episode should be shared withAbout Damon LembiDamon Lembi is a 3x bestselling author, the host of The Learn-It-All™ Podcast, and CEO of Learnit – a live learning platform that has upskilled over 2 million people. Drawing from his prior baseball career, Damon brings an athlete’s perspective to leadership. Through his journey, he has gained invaluable insights into what helps organizations grow, how great leaders learn, and why learn-it-all companies outpace their competitors every time.Resources and Mentions:Connect with Damon: https://www.linkedin.com/in/damonlembi/Download Damon’s book: https://BookHip.com/FTZRCJBCoach Steve Knudsen: https://www.facebook.com/steve.knudsen.9?mibextid=wwXIfrPodcast Contact Information:Website: www.learnit.comEmail: [email protected] us on LinkedIn and Instagram for updates.