Trailblazing #4 (07/01/2023)

What I recently found interesting:

Do we have to fear entrepreneurial failure?

Earlier this year I left my startup after leading it for 9 months. But even though I could easily describe the outcome as an entrepreneurial failure, I instead look back at it as a great learning experience that I was privileged to have in my first post-MBA year. Counterintuitively, I have actually grown significant confidence:

I had founded Cupola thru a venture studio because:

• I was unable to grow conviction in any of my own ideas,
• I was scared of going multiple months without a stable salary and had self-doubts about asking people for money (i.e. fundraise),
• I lacked audacity to go it alone and had insecurities about my skill set.

13 months after launching (and leaving) Cupola:

• I developed comfort in “no stable salary” life (i.e. to buy myself time and progress my professional life at my own pace I coach tennis, which also gives me a lot of satisfaction)
• I am more assertive and discerning about ideas and opportunities presented to me (i.e. I am able to distinguish between seeing a business opportunity thru the eyes of an investor and thru the eyes of an operator, with the latter being the one I would be excited to work on every day),
• I have a better understanding of what it takes to build a relevant product, how to grow the company organizationally, and how to lead a compatible team.

Tying my own experience back to the quoted research, if there is a small part of you striving to pursue entrepreneurship (i.e. if you enjoy brainstorming ideas and often find yourself wondering what it would be like to run your own firm), I would like to encourage you to take a full stab at it.

• Because even though, as human beings, we fear failure and it might feel safer to walk the traditional and familiar career path, the above article can hopefully alleviate some of the feared downsides, as it serves as an evidence that even an entrepreneurial failure (just like an entrepreneurial success) can lead to a faster career progression than climbing the corporate ladder.

I recommend reading the full paper (or at least the Introduction part), as it contains many generally interesting insights into career progression

• As a quick side note, there are probably plenty other papers suggesting that entrepreneurial failure sets you back a few years in your professional life; I do not intend to argue whom (and which data sets) to believe because at the end of the day the decision to pursue an entrepreneurial path is very personal; all I hoped to do was to offer you a counterintuitive (i.e. failure can lead to faster promotions) way to look at your career.

Venture studios, incubators & accelerators → what are the differences and similarities?

Generally speaking, I don’t think there is only one way to build companies. Many models have worked and each thriving founder will always have had their own unique reasons for why it was them who succeeded. Therefore, the only recommendation I have for an aspiring entrepreneur is to really get to know oneself and understand what kind of support (financial, strategic or operational) one wants and expects from the initial partners before choosing the vehicle to found a company (e.g. bootstrapping, search fund, friends / family / pre-seed VC investment, incubator / venture studio / accelerator); that decision should be treated like marriage and must be made with as much insight and precaution as possible.

Historical relationship between bonds and stock and its significance for broader economy outlook

This study done by my HBS professor, Luis Viceira, analyzes the relationship (as measured by Beta) between stocks and bonds over time and here are a few isolated takeaways:

• Interestingly, this relationship changes over time as it depends on many dynamic outside factors, which indicates the importance of deep understanding (and constant questioning) of the underlying reasoning behind certain conclusions instead of taking them for granted (e.g. bonds are a safe hedge against equities → the statement which is sometimes true, but as the study shows can also be false).
• While over time TIPS beta is expectedly more stable than its regular bond equivalent, as it controls for inflation and consequently has a clearer relationship with equities, it has recently spiked which may indicate the long-term (unrelated to inflation) downturn fears; the way I understand it is that there will not be a sudden economic crash, but there might be an unnecessarily long uncertainty and status quo in the market, inadvertently leading to a “behavioral waiting game” of who or what takes the risk and reinvigorates the economy first.
• Lastly, while analyzing data like this (i.e. when there is no clear right answer, as 2+2=4) there is always room for varying interpretations and differing viable and reasonable action plans to improve the economic situation; therefore the government policy that we, as individuals, will support comes down to how we view the world as a combination of our political, social and financial beliefs; and because of that, I think it is critical to be open-minded to other views and always go under the hood to seek the true reasons for why certain things are happening at the specific moment in time, and never settle for our traditional long-standing beliefs of the world.

Miscellaneous

Personal

I have spent June in California (OC, LA, SF) & Colombia (Santa Marta, Cartagena, Medellin & Cali) celebrating three friends getting married ?? and it was fun!

• Thru those weddings, life in its own natural way reminded me that frequently reconnecting with old and making new friends is an extremely important part of being a human as close relationships is what truly makes us happy
• Thanks to the weddings, I also had a chance to visit my “old stomping grounds” as well as explore new places, the combination of which made me deeply reflect on my future :)

Song Recommendation

• “Glycerine” by Bush -> I especially liked the sentiment behind the phrase “don’t let the days go by,” as it inspires taking action, driving toward one’s goals / dreams and fighting for what one believes in.
• As a bonus, I recommend listening to John McEnroe’s Commencement Speech at Stanford this year → I definitely found this very applicable to my life, especially his advice to be open-minded and constantly look for ways to reinvent oneself as well as his hope for people to be defined by something more than their professional lives.