Stories about conversations and the places that they take you.

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Cup 3 | Ligaya Tichy

Cup 3 intimidated me.

It’s a feeling I’m unfamiliar with when it comes to coffee.

She intimidated me the day I met her in Austin, Texas at the South by Southwest tech conference two years ago—and that was before I learned of the reputation she’d built as a Silicon Valley thought-leader on community building after playing a pivotal role in the early stages of successful startups Yelp and Airbnb.   

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When you meet Ligaya Tichy you immediately sense the passion and drive behind her caring personality, sharp wit and intrepid style.

My nerves led me to realize I hadn’t talked to many women my age in the first round of Cups. Furthermore, the women I did talk to weren’t in the tech space. The reason, I concluded, is it’s tough to write about phenomenal women without feeling inferior. I’d rather extol the accomplishments of someone chasing dreams significantly different than my own.

We met in a crowded coffee shop in San Francisco’s Financial District. Ligaya walked in wearing stylish black pants with edgy tears down the front. We ordered our coffee and found a cozy spot at large community table. Between sharing mutual friends, working in the same industry and having met before, launching the conversation was easy.

Born in Boston and raised in a small hippy town in Iowa, Ligaya studied Anthropology and International Relations at Tufts University. Working several jobs throughout college to pay her tuition, Ligaya didn’t have time to worry about what happened post-college. Although, even if she had, she likely wouldn’t have worried much. Ligaya is the type that trusts her intuition will lead her down the right path.

Without much foresight, Ligaya sold all her possessions after graduation and moved to Bali where her aunt had founded a birthing center in an area that had little access to developed healthcare. She was deeply moved by the experience, and several years later she became a certified doula, trained to help coach women through childbirth.

While still in Bali, but facing expiring visas, Ligaya and her boyfriend at the time discussed their prospects. They were big fans of House music and caught wind of the thriving House scene in San Francisco. A friend offered her couch as a landing pad so with nothing more than a backpack full of sarongs, Ligaya followed her intuition to a new adventure in California. With the little money she had, a coat and pair of pants purchased from goodwill, and a strong sense of determination and work ethic, Ligaya set out to find a job in the new city.

Close to a decade later, Ligaya’s life looks nothing like when she first arrived. In fact, she never imagined life would turn out so well—her enthusiasm and dedication led to a career many in the tech space only dream about. Soon after arriving in San Francisco she discovered and fell in love with Yelp, which at the time was a fledgling company. Ligaya relentlessly badgered the CEO for a job; declaring she’d sweep the floors if that’s what it would take to be a part of Yelp’s mission.

Yelp relented and offered her a operations manager role, which began her rise to becoming a well-known community builder in the Valley. Ligaya launched and developed several key markets for Yelp before leaving after four years to do the same for the housing rental site, Airbnb. When the community at Airbnb reached a stable level, Ligaya left and now enjoys a more balanced lifestyle serving as a mentor and investor for early-stage startups while spending plenty of quality time with her fiancé and dog.

When I met Ligaya in Austin she had an edgy haircut, bold lipstick and confident presence. I was a senior in college and remember thinking, I wish I had the courage to be so brazen and bold.

Sitting down to coffee with Ligaya was my chance to uncover the source of that confidence and enthusiasm—what emerged from our conversation was a thought-provoking look at careers, authenticity and the quest to live a meaningful life.

In her own words, Ligaya addresses the pressures of tough career choices (contains expletives).

Ligaya grew up in a progressive community and her passion and audacity may, in part, come from her father: a renaissance man with great artistic talent and strong opinions. It might also come from failed attempts at fitting in:

We were one of the only non-white families. My mom was Asian, my dad Czech. Even just having immigrant parents was different and I never fit in. I had a weird name that no one could pronounce (‘Ligaya’, she explained, rhymes with papaya).

I have a friend, Cici, who is Chinese and also grew up in the midwest. We talked about how when we were younger we wanted to have blond hair and blue eyes and just fit in. Well, you hit a certain point in your life where you just shrug it off because you know it’s never going to happen. I think this engendered an attitude of: well, if I can’t fit in why even try?

Despite that viewpoint, deciding to ignore the status quo was easier in theory than practice. The internal conflict that exists between the desire for self-expression and the fear of rejection is incredibly strong—regardless of outward confidence or attitude. Ligaya was not immune to the challenge of being authentic in a world filled with social norms and outspoken critics—but she shared a viewpoint that revealed the magic of being courageous and letting your true self shine:

If we want to keep evolving as a people we should let a little piece of ourselves out so that we can see how other people respond, so we can question our own assumptions, so we are able to evolve in some way. There’s a point where you just say it’s worth the risk. You know?

It is a really tough thing. I think it gets better as time passes; not as you get older, it’s not a perspective thing, it’s just that as you start to form relationships with people that are deeper, people you know and trust love you for you, it allows you to go a little bit further with that person. And in going deeper with that person, a little more of you comes out each time.

If you only spend time with those people, you almost can’t help but grow into who you are because when you’re with people you really love and that love you, it makes you want to share the real parts of you. It’s a good testing ground—a good practice—for being that version of yourself all the time.

It was during this explanation that my intimidation turned to appreciation. In all the coffee conversations I’ve had I’ve never directly touched on the power of relationships and the intimacy, trust, and vulnerability that happens within them—something I don’t think people talk about often enough.

Ligaya is an insightful, articulate and compassionate force. Our conversation had many topics that resonated with me: the importance of approaching life with enthusiasm, dedicating oneself to meaningful work, not being swayed by the viewpoints of others, finding a balance that makes you happy. However, it was this statement about being the authentic version of yourself that I found most meaningful.

The world is a scary place—for everyone. As Ligaya said, “Such is the human condition: suffering is inevitable”.

Regardless of wealth or success, we all wrestle with fears and insecurities. We all want to make a meaningful contribution to the world and fulfill our potential. We want to be loved and appreciated for who we are deep down.

But these hopes and desires are so raw and scary we often keep them bottled inside where they feel safe. We look around at successful and confident people (or the seemingly perfect lives we see on social networks) and decide it’s best to hide away the shadowy parts of our personality and only present our own confident and successful parts. It’s the fear of being vulnerable in an often harsh world.

This is ok to some degree, the raw parts of ourselves should be reserved for those that have earned our trust, not broadcast to the world.  

As Ligaya said, finding someone, or a group of someones, that you trust love you for you creates a safe space to slowly reveal the authentic self that hides behind the social mask. This takes courage, a lot of courage. But to be vulnerable with trusted friends, family or a significant other can lead to an incredible source of power: to reveal a deeper part of yourself and receive love and acceptance in return is life-changing. Especially because as you become more comfortable being authentic around close friends, you become more comfortable being authentic all the time. And this world could use more authenticity.

Plus, you create stronger relationships with those around you:

It’s a universal thing—the deeper you get to know someone the more you realize they are struggling with the same things. And that’s actually another reason to talk about what you’re going through and talk about what you think. In a way it can be very liberating for people because they go, Oh I’m not alone in thinking this. I’m not alone in feeling this or hating this particular thing about myself. Like you said, you find strength in solidarity around these things.

I was intimidated by Ligaya because I compared her history of achievements to my inner insecurities, She’s incredibly talented and successful, why would she want to talk to me?

I know she’ll cringe when she reads those words because Ligaya doesn’t care about titles or accomplishments. Ligaya cares about people.

It is that compassion and drive to understand what makes people tick that has led her to a successful career building communities. Ligaya understands that we as humans are wired to connect and that through connection and community we create opportunities to support, educate and celebrate with each other; to become better humans that create a better world.  

But first, we must find the courage to connect. 

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Cup 46

Person: Bo Fishback 

Drink: Regular coffee in a Kansas City coffee shop 

Bo Fishback is the self-proclaimed luckiest man in the world. 

By age 30, he had found his dream job. He worked as the president of Kauffman Labs for Enterprise Creation in Kansas City, Missouri where his main task was allocating $100 million dollars a year to various entrepreneurial projects. It was a job that was easy to love and one he saw himself in for another 20 years. 
 
Then one Monday in February, he walked into work and announced his resignation—effective immediately. 

The news came as a shock to Kauffman. It probably came as a shock to Bo too—when he left work on Friday he had every intention of returning the following Monday. But life intervened. 

At the insistence of his good friend, Eric Koester, Bo went to Los Angeles where he competed in a 54-hour Startup Weekend Event where he pitched an idea that had been rolling around the back of his mind for a while. It was a last minute choice to pitch and the decision paid off—not only did Bo’s team win, they attracted the attention of investors (including Ashton Kutcher) and raised nearly a million dollars overnight. 

… 

He explained this as we sat sipping coffee at the coffee shop in Kansas City, which is a five minute walk from the headquarters of Zaarly—one of the fastest growing, most-talked about startups of the year. In just seven months, they’ve scaled their product, assembled a dynamic team and left a noticeable impact on cities nationwide.  

According to CrunchBase, Zaarly is a location based, real-time buyer powered market. Buyers make an offer for an immediate need and sellers cash in on an infinite marketplace for items and services they never knew were for sale.

The format for a Zaarly is: I’d pay ____ for  ____. 

  • I’d pay $30 for someone to mow my lawn. 
  • I’d pay $45 for a ticket to this weekend’s Tigers game.
  • I’d pay $600 for a treadmill in good condition. 

The idea is to build a marketplace where people acquire goods and make money using technology and the communities around them. The young company has already generated over $3 million dollars in Zaarly transactions. 

It could, in theory, change the way business is done—become the next $50 billion dollar company. 

That is Bo’s vision and the reason he could walk away from the greatest job in the world without second thought. He didn’t want to watch someone with the same idea make it big while he sat on the sideline and watched. 

Now he and his team are working around the clock to make it happen. And from the looks of it they are succeeding

It helps that Bo (and his two co-founders) are no strangers to the entrepreneurial world. Bo has two successful startups under his belt: Orbis Biosciences, a drug delivery and particle fabrication company, and Lightspeed Genomics, a next-generation genome sequencing company (source: CrunchBase). In addition to these two companies, Bo has served as anadvisor, board member, and angel investor to many other ventures. 

Bo always knew he would start a company. When he was four years old, his father—and role model—left his job as at a hospital to start his own company selling respiratory therapy supplies. As Bo grew so did the company. By the time he was 18, his father sold his company and retired comfortably. Watching his dad run a business instilled the entrepreneurial bug in both Bo and his brother who is also a successful entrepreneur. 

However, at age 18, Bo didn’t expect he would be in the position he is in today. Bo grew up in a small Georgia town where he drove 50 miles to and from school. By the time senior year rolled around his top concern was finding a school outside of Georgia where he could play basketball (he’s 6’8”) and meet girls. He ended up at Southern Methodist University and while his basketball career was short-lived, he did meet his wife (and now mother of their newborn baby boy). 

After earning a degree in Medical Biosystems, he went to work for a corporation that basically gave him a budget and said go start a new branch for our company. He met their expectations. By the time he left, the team he built had over 200 employees. He then started his own company that (in what he calls a complete stroke of luck) sold within eight months. He decided to pursue an MBA and headed to Harvard Business School where he once again rolled out a successful venture. That’s how he garnered the attention of Kauffman and landed a job helping other startups. 

His motive for serial startups is simple, “I just like to build shit”.

And he gets lucky. “I’ve had so many experience where luck was on my side, I’ve reached a point where I just assume I’ll be lucky.”

Of course, the harder you work the luckier you get. And Bo works hard.

Although you wouldn’t know it if you met him—he’s easygoing with a propensity for fun. He’s also tall, charismatic, optimistic and a visionary.

That combination creates a rare ability to attract talented individuals and motivate them to accomplish a common goal. He’s so good his inbox is filled with hundreds of resumes applying for jobs that don’t even exist. One guy actually offered to pay to work for the company (it worked, he now works at the San Francisco office—and gets paid).
In all honestly, after Bo took time out of his busy schedule to sit down and have a genuine conversation with me I could have been convinced to relocate my life to KC and join the team.

I wouldn’t have been the first MSU kid to do it. Zaarly worked its magic on my three of my close friends (which is why I was visiting Kansas City in the first place). In March, my friend Eric met Bo through a project—Bo left a big impression on Eric and eventually offered him an internship at Kauffman. When Bo left Kauffman for Zaarly, it was easy to convince Eric to follow suit; he knew working with Bo would lead to something big.

When they company needed more interns it wasn’t hard for Eric to recruit his MSU classmates. Bo could offer them something that is hard to find: a chance to create something meaningful. If Zaarly works, it will change lives around the US and possibly the world.

It’s a big vision—and Bo thinks it’s going to work—but  even if it doesn’t, it will have been an incredible ride; an exciting chapter of life they can look back on as a reminder they were willing to take a risk to create something great.



I took a lot away from Cup 46—but what I will remember most is Bo’s optimism and vision.

Everyone is capable of finding that once-in-a-lifetime idea or opportunity that captures their heart and changes their life (and the lives of others). That risky idea that somehow doesn’t seem risky at all. An idea they can’t get off their mind. An idea that creates meaning and purpose.

But sadly, not everyone knows they have this capability.

Bo says he’s lucky—but it takes more than luck to stumble into a dream job, twice. I asked him what made him different from those that don’t find meaning.

"I surrounded myself with good people".

Coffee with Bo was fantastic from start to finish, but this part of the conversation really hit home. The night before, Eric and I were talking about how lucky we were to be pursuing exactly what we wanted to be pursuing when so many of our former classmates were finding themselves in lackluster jobs. When Eric found Zaarly he knew with 100 percent certainty it was the right choice for him. That is how I felt when I decided to go to Europe after graduation. We couldn’t explain the logic that led to our the decisions, but we both had a gut feeling that told us it was the right thing to do.

I told Eric I wished more people realized how much potential they truly have—realized they could be doing exactly what they love.

My conversation with Bo helped me see that we need good people in our lives to help us discover our potential.

I had to have coffee with two dozen people before I believed I was capable of spending two months in Europe post-graduation. Eric is more efficient. It took him one conversation with Bo—a man for whom he has great respect—to realize he could have a great impact on Zaarly if he relocated to Kansas City and joined the team.

In this crazy world of expectation and uncertainty it is way too easy to get caught in a maze of self-doubt and insecurity. That’s why it’s vital to find positive people that help us navigate our way through it.

Bo, who is incredibly talented, succeeded because he found people that helped him maximize those talents. That’s why he’s the luckiest man in the world. It’s also why he’s devoted to Zaarly. It’s a platform to inspire and create meaning for others—to pay it forward.


Cup 46 a testament that that a life filled with meaning, laughter, love and fun is possible for everyone. It takes a lot of work to make it happen, but it’s possible.
If you don’t believe that, surround yourself with people that do. Their contagious optimism and support will lead you to that dream job.

Then when you find it (and don’t settle until you do) reach out and help someone else. Whether it’s being a mentor to a young college student or a co-founder of a company that starts a movement.

Or better yet—both.

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