Jess Ma on Entrepreneurial Success, Failure, and Finding Balance

Jess Ma is an extraordinary entrepreneur who has co-founded over 10 companies collectively valued at more than a billion dollars. In this candid conversation with Eric Ries, Jess opens up about her entrepreneurial journey, including the highs of success and the lows of failure.

Jess shares that in the past year alone, she's had three companies not work out, resulting in millions of dollars lost. She emphasizes the importance of being comfortable with failure and making mistakes, noting that happiness and satisfaction should come from within rather than external circumstances.

The Reality of Entrepreneurial Success

Jess points out that when we listen to successful entrepreneurs, they often only talk about their wins and not their failures. She believes it's crucial to be open about both:

"I lost millions of dollars this year from my failures, Eric. And I'm glad that it was millions of dollars spread across many, many different projects trying to be as lean as possible to derisk and fail fast, but it's inevitable."

This honesty about failure is refreshing in a world where success is often glamorized. Jess argues that there's an art to getting comfortable with failure and making mistakes.

The Mental Health of Wealthy Entrepreneurs

Eric brings up the topic of mental health among successful entrepreneurs, noting that many seem miserable despite their wealth and success. Jess agrees, stating that most people, wealthy or not, are struggling with something.

She shares her own experience of having tremendous PR success early in her career, with TechCrunch calling her "the next Mark Zuckerberg." However, behind the scenes, her startup was struggling:

"My startup was not working out at all, Eric. It was just terrible. Like I was bringing in no revenue. Didn't have any metrics to justify the valuation that we were breaking."

Jess emphasizes that this contrast between public success and private struggle is common among entrepreneurs.

The Gift of Failure

Interestingly, Jess now sees her failures as a gift. She believes that unlike some entrepreneurs who experience immediate success, her journey of ups and downs has helped keep her grounded:

"I've had the gift of having tremendous failures and setbacks along the way. That's probably the best gift, unlike say Mark Zuckerberg where it was just like straight up to the right. I just had like so many screw-ups, lots of businesses that didn't work out."

These experiences have humbled her and taught her valuable lessons about resilience and authenticity.

Building Genuine Relationships

Jess highlights the importance of building genuine friendships and a real community. She calls these "chicken noodle soup friends" - relationships that feel nourishing and authentic, not based on success or status.

She also mentions the value of stepping outside the tech echo chamber, spending time in different environments, and gaining new perspectives.

Taking Care of Mental Health

Jess emphasizes the importance of self-care for entrepreneurs. She mentions finding a meditation practice and working out daily as crucial components of her routine:

"Finding a meditation practice, working out every day... the basics that we kind of forget about when we're in the egoic rush of building and trying to make money and have success."

She notes that once entrepreneurs start taking care of themselves and focusing on what truly matters, success often follows naturally.

The Myth of Hardcore Entrepreneurship

Eric and Jess discuss the common misconception that entrepreneurs need to be "hardcore" and neglect self-care to be successful. Jess argues that this isn't true based on her experience:

"Having some of those people I could point to... that matters, and unfortunately, I think the media promotes the role models who are like, you know, have no work-life balance or grinding it out."

She suggests that surrounding oneself with balanced, successful people can help change this perspective.

Curating Your Network

Jess shares her strategy for surrounding herself with the right people:

"That's why I organize so many events and dinners and do a lot of this hosting. It's really my cheat code for curating the people I want to surround myself with."

She emphasizes the importance of being intentional about who you spend time with, as it significantly impacts your mindset and success.

The Dangers of Short-Term Thinking

Eric brings up the issue of short-term thinking in business, particularly in Silicon Valley. He mentions the example of Silicon Valley Bank's implosion, which resulted from lobbying for riskier bets that ultimately led to the bank's downfall.

Jess agrees, noting that this short-term, exploitative mindset is prevalent but ultimately destructive:

"We have this like bizarre culture in business where it's like the more you exploit, the more you're tricky, the more you do this and that... the tougher and stronger you are, when in fact those are the very weaknesses that eventually allow someone else to out-compete you."

Talent Identification and Partnership

Jess is known for her ability to identify and recruit talented partners for her various projects. She shares her process, which involves extensive searching and a 90-day trial period:

"We will talk to dozens and dozens of potential people who could be the right fit for this company... Eventually I'll spend a full day or two days with finalist candidates, and even then we're doing 90-day plus trial periods."

She emphasizes that this process often doesn't work out, but it's crucial for finding the right fit.

The Importance of Continuous Learning

Jess discusses her approach to learning from failures and constantly improving her process:

"Every time we have something that does not work out... I sit down with my talent team and everyone else, I'm like, 'All right, like what did we learn here, what went wrong, how could we have caught this earlier?'"

She sees each failure as an opportunity to refine her approach and get better at identifying the right partners.

Being a Female Founder

Jess talks about her experiences as a female founder, including both the challenges and advantages. She mentions creating support groups for female founders:

"I love the female founder community. I've got a group I put together called badass female founders. It's a few hundred women."

She also discusses providing support for women who have faced harassment or discrimination in the industry.

Going "Full YOLO"

Jess shares her experience of deciding to go "full YOLO mode" in her life and business decisions:

"After my boyfriend in 2021 passed away, I gave myself permission to fully just do whatever I wanted to do in business and life."

This included buying luxury items, naming her investment company after herself, and generally being less concerned about others' opinions.

Dealing with Public Criticism

Jess discusses how she handles public criticism and negative comments:

"If you don't have my phone number, if you're not my friend, I don't really care about what you think."

She emphasizes the importance of not taking criticism personally and recognizing that it often says more about the critic than the person being criticized.

The Value of Early Tech Education

Jess shares her experience of attending computer camp at age 10 and how it impacted her:

"I loved computer camp. Yeah, I learned how to program at computer camp... Programming teaches that skill set in a low stakes way. And it also creates patience."

She believes early exposure to programming can teach valuable skills like structured thinking and problem-solving.

In conclusion, Jess Ma's journey as an entrepreneur offers valuable insights into the realities of building successful businesses, dealing with failure, maintaining mental health, and finding balance in life. Her candid approach and willingness to discuss both successes and failures provide a refreshing perspective on entrepreneurship in the modern age.

Article created from: https://www.youtube.com/watch?v=ltd3Bn5ZSgA