#219 Sihame El Kaouakibi: How to Fail Spectacularly—Then Win Even Bigger – Part One

Christopher Quek wasn’t built to follow the family script. In this two-part series, we explore how he walked away from the comforts of a well-established family business in Singapore to chase entrepreneurship in Malaysia—much to his father’s dismay. After returning home, he doubled down on his independence by selling his inheritance to launch TRIVE, a venture capital firm built on his own vision. Last episode looked into his quest for self-identity—the reasons behind his bold moves and how he made them a reality. This time, we’ll discuss his current work as a VC investor, his ambitions for the entrepreneurial landscape in Southeast Asia, and his thoughts on legacy and family at this stage in his life.Key Highlights of Our Interview:Kicking off with a big question: Is Singapore still relevant after 50 years? Here's an entrepreneurial view"In 2015, when Singapore celebrated its 50th birthday as a nation. Singapore evolved itself out of necessity where it built a whole nation, a workforce of engineers, scientists, bankers, lawyers, doctors, specialists. We started losing a whole generation of entrepreneurs."Bridging the Generation Gap: How to Turn ‘Parents’ Old Ways’ into a Future-Proof Family Business"I actually have a network of over 300 family business owners across Southeast Asia. And there's always this common themes that starts first.  Number one, how do I talk to my parents? How do I have a good working relationship with my parents and a family relationship back at home?  Number two, I don't like the way that my parents are doing things and I need to transform this business. How do I convince my parents that I can transform this business as well?"Turning Spare Millions into Family Business Magic: The Synergy Cycle of Tech, Money and Southeast Asian Economy"Everyone gets to have food on the table. What we didn't realize that what this family business did was that it took that technology, have more food, more quantity, and decided to sell it cheaper to a poorer province, where those villagers were now able to obtain more quantity of food for their families."Breaking the Patriarchal Mold: How Self-Development Earned Me My Father’s Respect"My father has been an Asian patriarch with an iron fist. He now talks to me about the side businesses that he's doing. He asks me as his advisor and no longer sees the son on whom he used to look down."Still Figuring It Out: The Never-Ending Saga of Self-Discovery"I still believe that I'm evolving. I'm still learning more in terms of understanding my identity."Fatherhood and Fortune: What’s the Game Plan for Your Next Generation, Chris?"Anybody who wants to help the next generation is to be a mentor of values rather than a mentor of processes."_____________________Connect with us:Host: Vince Chan | Guest: Christopher Quek______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

Christopher Quek wasn’t built to follow the family script. In this two-part series, we explore how he walked away from the comforts of a well-established family business in Singapore to chase entrepreneurship in Malaysia—much to his father’s dismay. After returning home, he doubled down on his independence by selling his inheritance to launch TRIVE, a venture capital firm built on his own vision. In this episode, we dive into his boldest moves, his pursuit of self-identity, and what it really takes to break free from expectations.Key Highlights of Our Interview:Father’s Furious Expectations: When a Third-Gen Heir Sneaks Out of the Family Business"I couldn't stand all the pollution that the manufacturing plant was producing. And finally, after three days, I sneaked back to Singapore and my father saw me. He got angry. He shouted at me."Family Education 101: Learning P&L Over Dinner with Dad, Where Burgers Come with a Side of Calculating Profits"He would take me out to restaurants. And he forced me to start calculating out the revenues. He will start telling me like, what do you think is the expenses behind this? And I had to start learning a profit and loss statement just by that very visible conversation itself."Beyond the Textbook: How Mentorship Shaped Chris' Evolution"I'm a product of my mentors in my life. So I'm the number two and number three mentors were also very successful businessmen."Owning My Identity: Mr. Quek or Just Mr. Quek’s Son?"There was already a trigger point in my value system that was I going to continue as a the next generation of business owners to continue polluting, just to make money for the sake of money."Finding My Way: From Circumstances to Self-Fulfilment"It was more of circumstances and situations and opportunities that just appeared.  If you ask me like some certain crossroads in my life, for example, heading off to Malaysia instead of China I felt that was the right thing to do."The Adventure of Self-Discovery: Uncovering Hidden Layers of Yourself at Every Stage"Give you a little bit of the element of what at every stage is about really discovering yourself, which is really an exciting journey. You don't realize that you have actually a lot of things about yourself that you haven't discovered. "_____________________Connect with us:Host: Vince Chan | Guest: Christopher Quek______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

Part Two. From politics to entrepreneurship, Sihame El Kaouakibi has faced—and conquered—some serious challenges. Burnout? Check. Bankruptcy? Been there. A political storm? Handled. But instead of breaking under pressure, she calls herself “anti-fragile,” using adversity as fuel for reinvention. In Part One, we explore how she built herself back up as a leadership coach, diversity advocate, and creator of Women Leaders OS. And this is just the beginning.Key Highlights of Our Interview:Burnt Out, Bankrupt, and Back in Business“I went from being burnt out, confused, overwhelmed, and even bankrupt to now being in the best shape of my life—physically, mentally, and professionally.”Validation Detox: Kicking the Need for External Approval“Without success, without my work, without external validation and recognition, I felt like nothing. I felt nobody.”Politics 101: When Ego Meets Reality“I made an ego-driven decision, and it was a messiah complex, believing I had everything—like potential and talents to drive change.”“I wasn’t aligned with my values and beliefs anymore. So my lesson is if you feel you have to give up on your principles, quit.”Thriving vs. Surviving: Why “You’re Not Stuck, You’re Just in the Wrong Pot” Applies to Your Career“The most liberating decision can be to move on and find your tribe, find your environment where you can thrive.”“Sometimes it’s better to accept the rejection than feeling stuck. Rejection can be redirection, and it’s sometimes better to just leave.”Operating System for Women Leaders: How to Handle Life’s Curveballs Without Crashing“My mission is to help 1 million women turn life challenges into life changes for the better. These women want to break through in their careers, but they want to do it without the burnouts.”“Women still lack internal beliefs and also support systems. So it starts really with women deciding that they are worthy and willing to change.”Success Isn’t Always Instagram-Pretty: The Ugly Side of the Hustle“There’s so much about glamorized success, but there is always another side. People you envy might be in deep pain, even if they are millionaires or have social status.”_____________________Connect with Us:Host: Vince Chan | Guest: Sihame El Kaouakibi______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

From politics to entrepreneurship, Sihame El Kaouakibi has faced—and conquered—some serious challenges. Burnout? Check. Bankruptcy? Been there. A political storm? Handled. But instead of breaking under pressure, she calls herself “anti-fragile,” using adversity as fuel for reinvention. In Part One, we explore how she built herself back up as a leadership coach, diversity advocate, and creator of Women Leaders OS. And this is just the beginning.Key Highlights of Our Interview:Burnt Out, Bankrupt, and Back in Business“I went from being burnt out, confused, overwhelmed, and even bankrupt to now being in the best shape of my life—physically, mentally, and professionally.”Validation Detox: Kicking the Need for External Approval“Without success, without my work, without external validation and recognition, I felt like nothing. I felt nobody.”Politics 101: When Ego Meets Reality“I made an ego-driven decision, and it was a messiah complex, believing I had everything—like potential and talents to drive change.”“I wasn’t aligned with my values and beliefs anymore. So my lesson is if you feel you have to give up on your principles, quit.”Thriving vs. Surviving: Why “You’re Not Stuck, You’re Just in the Wrong Pot” Applies to Your Career“The most liberating decision can be to move on and find your tribe, find your environment where you can thrive.”“Sometimes it’s better to accept the rejection than feeling stuck. Rejection can be redirection, and it’s sometimes better to just leave.”Operating System for Women Leaders: How to Handle Life’s Curveballs Without Crashing“My mission is to help 1 million women turn life challenges into life changes for the better. These women want to break through in their careers, but they want to do it without the burnouts.”“Women still lack internal beliefs and also support systems. So it starts really with women deciding that they are worthy and willing to change.”Success Isn’t Always Instagram-Pretty: The Ugly Side of the Hustle“There’s so much about glamorized success, but there is always another side. People you envy might be in deep pain, even if they are millionaires or have social status.”_____________________Connect with Us:Host: Vince Chan | Guest: Sihame El Kaouakibi______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

Higher education often feels like a reality TV show—full of rivalries, dramatic eliminations, and schools fighting for the top spot. But what if universities actually worked together?Enter Dr. Bridget Burns, CEO of the University Innovation Alliance (UIA) and host of The Innovating Together Podcast. From her small-town roots to becoming a driving force in educational reform, Bridget is on a mission to replace academic competition with collaboration. She’s tackling the “Higher Ed Hunger Games” head-on, working to boost graduation rates and open doors for low-income students—no cutthroat eliminations required.Key Highlights of Our Interview:Who Actually Likes Change? Spoiler: No One“Everyone who says they like change is a liar. You only like change that is your idea and that you actively participate in creating.”30:07—Mending Hearts in the Office: When Leaders Turn into Heartbreakers"There are a lot of people walking around with broken hearts because they’ve had a leader who’s betrayed them."33:39—The AI Rat Race: Why Can’t We All Just Get Along?"This natural tendency to compete with each other. There’s like an arms race and that’s what’s happening with AI.”38:41—From Cap and Gown to Capable and Grown: Reinventing the Grad-to-Gig Highway"There should be coaches for faculty to embed career readiness into every single classroom, starting from the first class a student takes."______________________Connect with Us:Host: Vince Chan | Guest: Bridget Burns______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

Higher education often feels like a reality TV show—full of rivalries, dramatic eliminations, and schools fighting for the top spot. But what if universities actually worked together?Enter Dr. Bridget Burns, CEO of the University Innovation Alliance (UIA) and host of The Innovating Together Podcast. From her small-town roots to becoming a driving force in educational reform, Bridget is on a mission to replace academic competition with collaboration. She’s tackling the “Higher Ed Hunger Games” head-on, working to boost graduation rates and open doors for low-income students—no cutthroat eliminations required.Key Highlights of Our Interview:Overcoming Adversity: Bridget's Journey from Isolation to Empowerment“I grew up in a cul de sac of racism, homophobia, misogyny—very rural America—and getting out was super important.”Problem in Universities: Unveiling the Diffusion of Innovation Problem“We don’t know if what we’re doing is any good, or how to scale it.”Higher Ed Hunger Games: Tackling the Cutthroat Competition"Higher education is highly competitive, hierarchical, set up to pit you against others, which leaves very little space to share about shared problems."Real Change or Just for Show? Scouting for True Innovators in Academia"We need to figure out who else is a worker bee, who's interested in doing the really hard stuff and not just drawn to the image."Who Actually Likes Change? Spoiler: No One“Everyone who says they like change is a liar. You only like change that is your idea and that you actively participate in creating.”______________________Connect with Us:Host: Vince Chan | Guest: Bridget Burns______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

Change isn’t just a business buzzword—it’s a way of life. Jason Bloomfield, Global Head of Change and Experience Design at Ericsson, has spent over 20 years navigating the twists and turns of M&A, corporate transformations, and direct-to-consumer strategies. But his most valuable lessons didn’t come from boardrooms—they came from life itself. From childhood challenges to corporate shake-ups, Jason shares how resilience, adaptability, and a little bit of humor can turn even the toughest transitions into opportunities.Key Highlights of Our Interview:0:36—It's All About Giving Back4:02—From Upper Middle Class to Crash Course in Adulting: Why Unwanted Life Experiences Can Be Your Best Teachers“I was in the middle of high school, where focus on study really needs to ramp up. Instead, I was learning home economics by necessity and dealing with my parents’ rapidly deteriorating relationship.”14:04—Building Resilient Relationships: Navigating Anxiety and Fear During Mergers & Acquisitions17:26—Being human: How is it possible to scale empathy to 100,000 people across 180 countries?24:44—Navigating Company Pride: When Heritage Turns into Hurdles“It’s quite a thing to come into a company that has 140, 150 years behind it. Pride can at times obscure a line of sight on the way forward.”31:11—Asking the Right Questions: The Surprising Reasons Retirees Didn’t Want to Go Paperless“We thought retirees were less digitally comfortable, but it turns out it was a trust issue—without something physical, they feared companies might alter their records behind the scenes.______________________Connect with us:Host: Vince Chan | Guest: Jason Bloomfield______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

What do Tintin and talent recruitment have in common? Just ask Ian Myers. As founder and CEO of Oceans, he’s on a mission to connect Sri Lanka’s top professionals with U.S. businesses—scaling his company from zero to $10 million in just two years. But his career isn’t just about business; it’s been a full-blown adventure. From banking and venture capital to gaming and entrepreneurship, Ian has navigated industries (and continents) with one simple rule: trust your gut and keep moving forward.Key Highlights of Our Interview:Why Tintin Beats Tech Titans: Ian’s Unconventional Role Model“My role model is Tintin. He’s always up for an adventure, exploring new places, and embracing different cultures. That’s the kind of life I want to live.”Zen and the Art of Leadership: How Buddhism Shaped My Approach to Chaos“Buddhism has a lot of excellent teachings that are applicable to running a business… It’s at its core, a method of grounding yourself through honesty in your reality and the potential of everything around you.”Comparison Anxiety: Why Scrolling LinkedIn Might Be Ruining Your Life“I talk to young people today, and they’re always comparing themselves. They’ll say, ‘Oh, this person who went to my college is now a vice president. My life is ruined.’ I’ve never really worried about my career; I just follow what’s interesting.”Experiencing Ageism Across Cultures: From Japan to CEO at 26“In Japan, age almost becomes the most important thing about you—your track record and success play a much smaller role. That was something I couldn’t personally tolerate.”Skeptical by Nature: Why Ian Questions AI Hype“The technology is impressive and important, but like most great innovations, the adoption curve will likely be much longer than people expect. If you look back at tech predictions, the timeline for changing the world is almost always too short.”Connect with us:Host: Vince Chan | Guest: Ian Myers______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

So you finally quit that toxic job, only to find yourself in another workplace filled with the same drama. What gives? Leadership expert Jennifer Selby Long explains why office politics follow you wherever you go—and how to stop them from running your career. In this two-part series, we tackle power dynamics, corporate chaos, and the real reason some people seem to climb the ladder effortlessly while others get stuck. If you’re tired of feeling like a pawn in someone else’s game, this episode is for you.Key Highlights of Our Interview:Talent vs. Tactics: Why Performance Alone Doesn’t Guarantee Success“In corporate environments, it’s often not the most skilled or hardworking employees who thrive—it’s those adept at navigating office politics. Top performers may drive results, but their brilliance can threaten insecure leaders, creating a system where political tact outshines true talent.”The Right Culture for the Right Person“Some thrive in competitive political environments; others find them draining. The key is identifying whether your personal interests align with the culture around you. The fit matters more than fighting a system that may not suit you.”No Permanent Friends, No Permanent Enemies—Just Interests“Drawing from the wisdom of Martin Luther King’s attorney, Clarence Jones: the game of politics is about aligning interests, not forging everlasting alliances. Understanding this can shift how you approach your workplace dynamics.”Burnout and Disengagement: The Fallout of Neglecting Talent“When talent is neither respected nor recognized, it creates a workplace rife with disengagement and burnout. Organizations lose not just individuals but the potential for meaningful progress, leaving behind a culture where playing the game matters more than delivering value.”_________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.

So you finally quit that toxic job, only to find yourself in another workplace filled with the same drama. What gives? Leadership expert Jennifer Selby Long explains why office politics follow you wherever you go—and how to stop them from running your career. In this two-part series, we tackle power dynamics, corporate chaos, and the real reason some people seem to climb the ladder effortlessly while others get stuck. If you’re tired of feeling like a pawn in someone else’s game, this episode is for you.Key Highlights of Our Interview:Finding Your Ally Among the Majority“In political environments, success hinges on securing a powerful ally. Aligning your interests with theirs and elevating them as a leader in your cause is essential if you plan to stay and thrive in such an environment.”When Conversations Clash, Progress Pauses“Business meetings often default to task-focused debates where differing perspectives turn into verbal standoffs. Rarely do teams pause to acknowledge the conflict and approach it constructively, missing opportunities to uncover deeper understanding.”No Permanent Friends, No Permanent Enemies—Just Interests“Drawing from the wisdom of Martin Luther King’s attorney, Clarence Jones: the game of politics is about aligning interests, not forging everlasting alliances. Understanding this can shift how you approach your workplace dynamics.”Assumptions: The Silent Saboteur“Most conflicts arise not from genuine disagreement but from unchecked assumptions about others’ motives or goals. Pausing to clarify and validate these assumptions can eliminate a significant portion of perceived conflict.”_________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long______________________--**Chief Change Officer**--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.6 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>100,000+ subscribers are outgrowing. Act Today.