New book from NYT bestselling author Lewis Howes is now available!

New book from NYT bestselling author Lewis Howes is now available!


Sukhinder Singh Cassidy

Building Wealth, Overcoming Failure & Rethinking Risk Taking


It’s time to think about risk-taking.

In the business world, you hear much advice about how vital it is to take risks to achieve your goals. About how taking a leap of faith will be the key to living the life of your dreams. But what if that’s not always the case? What if that approach to risk-taking doesn’t tell the whole story? What if every decision we make isn’t actually a “make or break” situation that will change the course of our lives forever?

The truth is that — unless you hit the lottery — the road to success rarely goes by one decision. Following it requires a thousand seemingly small choices. This mindset shift is SUCH a game-changer, and my guest helped open my eyes to it during our conversation.

In this episode of The School of Greatness, Sukhinder Singh Cassidy joins me to discuss how to build long-lasting wealth, rethink risk-taking, handle failures, and so much more. I’m excited to share this one with you all and think it will help you better understand how to apply Sukhinder’s abundance mindset to your own life. So if you’re ready, let’s get started!

Who Is Sukhinder Singh Cassidy?

My guest today is Sukhinder Singh Cassidy. She has an undergraduate degree from the Ivey School of Business Administration at the University of Western Ontario, Canada. For more than 25 years, she’s been a leading tech entrepreneur and CEO who’s grown, scaled, and advised for companies like Google, Amazon, and more. She’s currently the Founder and Chairman of theBoardlist, a talent marketplace focused on putting diverse leaders into key executive positions. She also serves on the board of directors at Urban Outfitters and Upstart

Earlier in her career, she served as the business co-founder of fintech pioneer Yodlee. She also served as a board member at Ericsson and Stitch Fix and as a strategic advisor to Twitter. As if all that weren’t enough, she is also a proven tech investor whose current and previous investments include Reformation, The RealReal, Sunbasket, Senreve, and more. Most recently, Sukhinder served as the leader of StubHub, the premier global consumer ticketing marketplace for live entertainment, which she and her team sold for $4 billion in February 2020.

She just wrote a new book called Choose Possibility: Take Risks and Thrive (Even When You Fail), where she shares the most valuable lessons she’s learned over her years of experience in leadership roles at some of Silicon Valley’s most well-known companies. Presently, she lives with her husband and three children in northern California.

Sukhinder’s story is so inspiring, and her insight when it comes to business and life is something I hope you find as much value in as I did. It was a real treat getting to speak with her, and today, I’m sharing the wisdom she shared with me!

Tips to Build Wealth Easily 

As a leading tech entrepreneur and CEO, Sukhinder is definitely one of the most qualified people to discuss various tips to build wealth. In our conversation, she shared two tips that I think will be really useful for all of you.

Tip #1: Go For Equity Ownership

Sukhinder strongly advises focusing on equity ownership as the main path to building wealth. She believes that the best way to make money is by owning a part of the company in which you are investing — whether it’s big or small. This way, your investment will grow along with the growth of the company itself.

“If you have equity in a big company or small company — whether you started it or not — you already have the key to wealth creation. It’s the very reason why people own their homes because homeownership is the biggest source of wealth for people.” Sukhinder Singh Cassidy

There are still many people who don’t understand how to build wealth on their own. This is what Sukhinder wants to see changed.

Tip #2: Save Early

I started investing in IRA and other investments when I was 27. At that time, I felt like I didn’t have that much to invest to save. But now, 11 years later, I’m definitely surprised at what I’ve accumulated. That experience made me realize that the best time to start saving is now. If you’re younger, all the better!

“Everybody knows it, but few do [it]. By saving early and waiting for compounding returns, it allows anyone to eventually become an owner of something.” Sukhinder Singh Cassidy

These two things, savings and ownership, are the critical building blocks to wealth. However, at times, many of us might wonder if these two tips are genuinely enough. Is this really how the wealthiest people of the world become so rich? What do they know differently than average or below-average earners? 

Sukhinder and I believe that it has something to do with the right mindset. If you want to build wealth and become financially secure, a good place to start is by learning from those who have already done it.

For Sukhinder, her father taught her the importance of building wealth when she was young. She grew up seeing her father save money and invest in a stock market.

“My dad owned equities. He owned stocks. I grew up seeing him call his broker and buy stocks every day. That was when I saw stock ownership as a thing.” – Sukhinder Singh Cassidy

This early experience is what opened her eyes to the importance of financial literacy. She believes that it’s vital to set one’s mind to have a healthy relationship with money. It’s what will get anyone off that mindset that money is filthy or that having it will make you evil.

She also advises her fellow women never to hesitate to have conversations about money, especially when in relationships. She suggests that money conversations with significant others should happen more often.

“Don’t be afraid to ask your significant other questions like, ‘Where’s our bank accounts? What do we have?’ It’s not just a question of being literate. It’s a question of being informed and not just trusting your financial decisions to other people.” – Sukhinder Singh Cassidy

Another important thing she emphasizes is how everyone should learn how to take risks. By doing so, you’ll learn when to cut your losses and know that every mistake is also a learning opportunity.

By learning how the wealthy amassed their wealth and being financially literate, you will build your own financial legacy. Learn from those who dared to invest time and money in building wealth instead of worrying about what others think. Remember that there’s no such thing as an overnight success. Don’t be ashamed to ask for help on your journey towards building wealth.

“If you want to build wealth, invest in what you know.” @sukhindersingh  

Overcome the Failure Mindset

In a person’s journey of building wealth, the fear of failing is also pervasive. I remember that as a speaker for almost ten years — and as one who has been making money on stages and talking to 20 thousand people — I still get afraid every time I go up the stage.

One day, I remember calling my coach hours before a speaking engagement and asking him why I was still nervous and afraid. He said that I’m worried because I was fearful of how I was going to look. I was scared of being embarrassed, not saying the right thing, or messing up. I was more afraid of those things than I was excited about being of service to the audience.

So in the process of helping me sort out these fears, we went through an exercise where he asked me what will happen to me if I ever mess up with my stage performance. From my answer, he followed up with a question of “Then what?” We just repeated the process until it made me realize that there’s always a choice to react differently.

This is related to how Sukhinder sees failure. For many of us, we see failure as if it’s the end of everything. This concept of failure is a myth she wants to debunk.

“First of all, you have to get out of this idea that you have one shot at glory. … Now, if you believe that what’s between you and a reward is probably not one decision, but 30, 40, a hundred, then it focuses on your ability to keep choosing. If you can keep choosing, you will find a path. You may not end up where you started, but there will always be a path for you to reach your goals.” – Sukhinder Singh Cassidy

What Sukhinder is suggesting is to look at success from another perspective. Think about it this way — success definitely not something that can be reached in an instant. To take steps towards building wealth, you should expect that your journey will have some setbacks. So when failure does happen, just realize that this is part of the process, and it doesn’t make you less of what you can be in the future.

She further advises that to deal with failure, one must always be in the failure-mode plan.

“I always say to people that if it’s a big risk, go for the failure-mode plan. This means think[ing] of the five choices you’d make after taking the risk.” – Sukhinder Singh Cassidy

Doing so allows anyone to come up with recovery plans that can be used when failure happens. It provides a sense that they are not just about making mistakes and learning from them. It’s also about living with a sense of certainty that even in the face of such failures, one will still be able to stand up again as a more aware person.

This also reminded me of the interview with a UFC fighter who talked about how they trained to be in the most uncomfortable situations. If they’re on their back with their hands held together by a guy who was punching them in the face, how can they get out of it? How can they stay calm? By thinking and training for these worst and uncomfortable positions, they can devise ways to get out of them.

Courage is not about being brave or tough all the time. It’s more about practicing to be in these situations so you would have a solution that works. So if you want to build wealth, don’t just try to build wealth. Practice becoming the type of person who can survive and thrive even in the worst-case scenario.

Rethink Risks

In setting out to build wealth, we might be afraid of the risks involved. But when we’re always focusing on avoiding failing, we have probably lost the game already. It’s because failure is a part of the learning-excelling equation.

Sukhinder knows this —she has taken multiple risks in her career. Some she has become successful with, some she hasn’t. Yet she chose to embrace them and try to think of new ways to approach them.

“To build wealth, you need to take a little risk. If you’re too afraid to manage all your money, take only 10% of it to manage this directly. Also, lessen risks by investing in what you know.”Sukhinder Singh Cassidy

Aside from this, she also wants to work on debunking the most significant business myth that rewards and risks are singular. She wants to show people that significant risks don’t always mean big prizes and vice-versa.

“People have to stop over-weighting the first choice. As long as you are willing to keep choosing, there are a thousand choices between you and success. … Keep aiming for impact in every single choice. Cumulatively, you will have an out-sized career, and you will have an out-sized life. … The people I know who succeed greatly are perfect master risk-takers as measured by small and big acts of possibility. It’s opposed to this one big act and possibility for which people think made them successful.” Sukhinder Singh Cassidy

Sukhinder only reminds us of something we might have known all along but usually neglect to remember: We can’t always expect a considerable risk that equates to high returns. Even if the first choice isn’t fruitful, we still have many more chances to try again. It doesn’t mean we have to stop, it only means that we need to continue moving forward. This could also be one of the keys to avoiding failed businesses and the suffering that comes with them.

Instead of anticipating everything that could go wrong, why not be okay with trying and pushing yourself out of your comfort zone? Focus on the big and small possibilities. As long as you keep working for what you want and without being afraid to fail, success will eventually come knocking at your door. More importantly, learning how to be agile and trying again and again on your way to results and greatness is more important than just trying to avoid risks at all.

So now that you are aware of all these ideas the next thing you should do is gather your courage and focus on building wealth! Remember, it’s the small things that matter and not just having one big act of possibility responsible for your success.

Why You Should Listen to This Sukhinder Singh Cassidy Podcast Episode Right Now…

T.S. Elliot said, “Only those who will risk going too far can possibly find out how far one can go. Jim Rohn said, “It doesn’t matter which side of the fence you get off on. Sometimes, what matters most is getting off. You can not make progress without making decisions.”

Many times in our lives, we might have hit a huge roadblock or found ourselves in a problematic situation that will require us to make a choice. It is only the first hard step when this happens, and further decisions can be made after that. Just like what Sukhinder shares, this means that we should not be afraid to take another risk. Although there are some risks out there that might be detrimental, there are also small risks that we can take on to build up the courage to achieve our greatness.

Speaking of, here is Sukhinder’s definition of greatness,

“I think it’s people who not only create impact in their own lives, but they create impact and possibility for others.” Sukhinder Singh Cassidy

This interview with Sukhinder is truly inspirational! She reminds us that even if there’s a significant amount of risk to pursue our dreams, we can be confident that it’s all worth it.

These precious insights that she shared with us today are found in her book, Choose Possibility. These are only a few of the many reasons you should read this book, so make sure to check it out here.

You can also connect with her through Twitter and Linkedin. Also, if you found her thoughts valuable and inspiring, don’t forget to tag me, @lewishowes, with your key takeaways. 

Lastly, if you enjoyed today’s episode, please subscribe to The School of Greatness over the Apple Podcasts and leave us a rating! Sharing is caring — it will help spread this message even further!

I hope that this interview with Sukhinder Singh Cassidy inspired you as much as it did me. If risk aversion has kept wealth out of your reach, I believe her advice could change the way you think. So make sure not to miss this full episode here!

To Greatness,

Lewis Howes - Signature

“When we can articulate our gifts, we can make a lasting impact.” @sukhindersingh  

Some Questions I Ask:

  • What are the biggest lessons that your father taught you?
  • How do you express your gifts in business?
  • When do you feel the most loved?
  • Is it possible to feel at peace in a high position business role?
  • Why do you think most businesses fail?
  • What did you learn about yourself during the pandemic?
  • What do you think are the 2 most important things for building wealth?

In this episode, you will learn:

  • The life-changing lessons Sukhinder learned from her father
  • Why most businesses fail and how to make sure your business isn’t one of them
  • Why we all need to change our mindset around failure & risk taking, and what to do instead
  • The best ways to start building wealth today
  • What Sukhinder considers the most rewarding experiences she’s had over the course of her career
  • Plus much more…
Connect with
Sukhinder Singh Cassidy

Transcript of this Episode

Music Credits:


Kaibu by Killercats

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