An Honest Opinion on Entrepreneurs |TechTrek Reflection

Entrepreneurs – a term usually associated in the media with deviants, massive risk takers, problem solvers, critical innovators, and garage startup hustlers turned Lamborghini drivers. Who are they really? Entrepreneurs are shaping incredible companies through hardship and vision.

Image result for elon musk early startup days
Elon Musk living off one dollar a day in college
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Musk later buying a McLaren F1 after his success with Paypal. Later wreaking the car on his way to work

Before the trip, I thought of my parents when I thought of entrepreneurs. My mom and dad met to start a tech company together. Contrary to the norm, my mom was my dad’s technical founder, and they set out to build a telecom company in Central New Jersey. With both parents as entrepreneurs, I lived through the instability, uncertainty, rapid growth and catastrophic event of a failed venture. To put it simply, life was a roller-coaster ride. As an indirect participant, I witnessed huge swings in the company, the loss of family friends, absent periods of parenting, fair share of stress and tears, and a handful of other hardships and confusions. I relocated 7 times during elementary school, living from Manhattan’s and Hong Kong’s high rises to worn down apartment in rural ShenZhen. During my teenage years, I questioned why someone would want to start their own company. In fact, to see it all over again with a serial entrepreneur as a father, I sincerely believed serial entrepreneurs were crazy and illogical.

They don’t think the way other people think. They see things from angles that unlock new ideas and insights. Other people consider them to be somewhat insane. – Justine Musk (Musk’s first wife)

“My proceeds from PayPal were $180M. I put $100M in SpaceX, $70M in Tesla, and $10M in SolarCity. I had to borrow money for rent.” – Elon Musk

Serial entrepreneurs seem crazy from an outside perspective, but they are incredibly insightful and driven individuals. My definition of an entrepreneur has tremendously deepened after my recent trip to California. I am far less afraid.

Setting the Tone

The first dinner with CJ Reim and Peter Bell set the tone for the trip. Both CJ and Peter accomplished so much and were so humble. They gave another deep dive of the VC space. The relationship entrepreneurs had with his or her VC was so important. The pairing of startup and VC resembled marriages. It was clear the VC business was a people’s business. The two mentioned the hard statistics of startup survival rates, and liquidation periods. On average, it took 8.4 years to determined whether a venture backed startup would prevail. With a success rate of 40%, the majority of founders walked away with nothing after a near decade. The dinner with Amity Ventures presented in vivid detail the landscape of today’s entrepreneurship.

The Guts to Chase and Change The Vision

Founders are adaptable visionaries who bare tremendous responsibility. From struggling startups such as Brava Home and Omni to giants such as Oracle and Facebook, the founders have been frequently tested in hardship to adapt a company’s priorities to the rapidly changing markets and customer demand. The founder holds absolute belief in a vision, yet needs to focus on better alternatives to gain long run competitive advantages. These pivotal moments put the founder, team, and product to the first survival test. Brava’s effort to figure out a product market fit was a perfect example. Mark Zuckerberg’s decision to make Facebook available to a broader user base, and Larry Ellison’s initiative to acquire small tech startups adding to Oracle’s products were founder initiative. Those moments explain the success stories today. Vision and execution trumps stubbornness. No wonder why investing in adaptable founder was a key factor in a VC’s investment decision.


The importance of timing would of been overlooked, though mentioned by VC, if we had not visited the Avachato, Brava, Wonolo, InstaWork Omni, Nuro, Fanatics, and Split. These visits really eliminated the naive notion of starting a company just to do so. The success of a venture backed startup was determined by the timing of matching a market opportunity. Split, Wonolo, InstaWork, and Nuro were ahead of Avachato, Brava, and Omni; on the other side of the spectrum, it was clear Fanatics was quickly maturing. This echoed the importance of a great team matching a great market.

Culture and Energy

A startup or company is a larger projection of the founder’s culture. From the inspiring founder cultures at Wonolo, Madison Reed, Split and ThredUp to the aggressive vibe at Sequoia, the underlying culture of a firm heavily influences performance under pressure. A quick comparison of InstaWork’s and Wonolo’s separate energy in the office can demonstrate the relative success and confidence of one another. I still get goosebumps thinking about Wonolo’s presentation. Yong Kim’s lonely yet heartwarming career story was undoubtedly inspiring. Madison Reed stood out as there was a disparity in the youthful energy of the firm, and the age of the founder. Amy Errett was sharp to answer questions, and her eye blazed with excitement and dominance. For larger firms, a consistent culture spreads to new employees as we saw in Facebook, Google, Apple, and Airbnb, providing support and guidance to employees as new challenges arise.

Move Fast, Breaking Things, and Shake Hands

Not all great entrepreneurs have great handshakes, but all successful ones can critical innovate and delegate tasks. As Pat Twomey mentioned last week, the first to join Uber thrived by innovating, adapting, and persevering constantly. While this competitive culture turned Uber to a global company, Uber would face challenges of diversifying and organizing its ranks leading to issues in 2017. Madison Reed had it’s hiccup when Amy Errett waited on a technical founder. For a startup to scale rapidly, founders need to shake the right people’s hands, bring them aboard, all while maintaining a heterogeneous team. Mike Liberatore and Doug Mack were critical hires, as Airbnb solved global payment and financial reporting issues and Fanatics’ global operations expanded.

The Path Ahead

While there are many cold emails and handshakes ahead, the future path is less daunting. TechTrek has transformed my view of entrepreneurs, and in turn made me question what I want to do with my life. Entrepreneurs made me realize a full pursuit of one’s calling is possible but difficult. The influx of capital from VC eliminated substantial personal risk which my parent took when they started a company. At a young age, I have less to lose if a startup goes belly up, yet conventional wisdom reminds me of the corporate job post graduation. The path a head is uncertain but exciting. In conclusion, TechTrek was an unforgettable experience, as it opened the door to work in tech space.

I am very grateful for going on the trip with motivated peers, Kelsey, Professor Kane, and Professor Doyle. It has been an unforgettable trip!

Really great memories in SF

5 thoughts on “An Honest Opinion on Entrepreneurs |TechTrek Reflection

  1. Robert that’s really interesting to hear that your dad is a serial entrepreneur and you experienced the roller coaster of start ups first hand. I can only imagine how that shaped your tech trek experience, but it’s great to hear that the trip made the future less daunting for you, I feel the same way after coming back.

    Liked by 1 person

  2. Great, meaningful post, Robert! Hearing your background prior to this class is so interesting, and I can only imagine the extent to which it shaped your experience. I really liked how you shared your appreciation for Wonolo, its story, and now mission. This was definitely one of my favorite companies, and I loved reading Young Kim’s post that shared in your blog. Hearing his story in person was absolutely one of the best parts of the trip. So great getting to know you!

    Liked by 1 person

  3. I love this reflection post, Robert! Your family story and your thoughts about entrepreneurship before and after the trip was different from mine own yet so refreshing. One of the things I love about this class/trip is that it did not force the idea of entrepreneurship down our throats, but instead opened doors for us and gave us more potential future paths. However, it did leave the most difficult choices for us. Whatever you choose to do in the future, I am sure you will do great!!

    Liked by 2 people

  4. Robert, this post was great. I felt like I was right there with you as your views on entrepreneurship changed! The story of your parents is very interesting and I’m sure they are a wealth of knowledge in this space. My favorite line from this post was “the path ahead is uncertain but exciting.” This whole post really resonated with me and reminds me of something Mike at AirBNB said, “The only thing that is certain is change.”

    Liked by 1 person

  5. Great post! I am also grateful that our trip to the Bay Area presented us a full story of entrepreneurship that is not limited to startups like Brava Home and Omni. Entrepreneurship also plays a role at Facebook, Oracle, and Salesforce. Even with the stats of 8.4 years and 40 percent failure rate in startups, I like how you concluded that “a full pursuit of one’s calling is possible but difficult”.


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