Breadth and Depth

Connecting others and with others through venture capital and medicine

Sherman Leung
3 min readSep 22, 2018
IMO, the ocean has the best T-shaped skillset in the world

For the last few months, I have been intensely deliberating a number of short-term and medium-term career decisions as I continue to discern my personal calling and career trajectory. As I apply to medical schools this cycle and more seriously explore venture capital as an associate in this last gap year, I’m sure my thoughts will evolve over time but I write this to give others (and my future self) a snapshot of how I’m sizing up this next year with purpose and intentionality.

PM to PM

Practicing medicine has been on my mind ever since starting college as a biochemistry major + premed. While an undergraduate, my interests in Computer Science and technology led me to the still-strong belief that there is so much opportunity to scale one’s impact in healthcare + medicine without serving patients as a physician. Jumping first into healthcare as a software engineer, and then into product management helped me pressure-test my evolving hypothesis about where now I believe the rate-limiting step of healthcare innovation to be — product-market fit challenges in an evolving and complex incentive landscape. Working on products at Mango Health, Muvr Labs, ConnectHealth and now PatientPing have allowed me to confidently say that the intersection of healthcare + product is a uniquely impactful and differentiated lens that I’m sure I will continue to consider and use throughout my career.

What calls me to medicine now, however, is this undeniable desire to work more closely with patients vs. serving them (and the broader healthcare system) through technology. Though I still believe that healthtech product management is a tremendous vehicle to broadly impact and serve many patients, I have found that the inability to care for a patient’s holistic needs beyond what technology can serve is something I cannot ignore. In the past year, I have taken intentional steps to continue validating this interests through shadowing in multiple Boston EDs, taking the MCAT, and volunteering for truly inspiring organizations like Boston Healthcare for the Homeless and HMS’s Family Van. Formative experiences in seeing and caring for patients, the intellectual challenges of (re)learning biological pathways, and the joy of directly connecting with and interceding for another human’s well-being’s seems to satisfy the depth of patient interaction I have been missing. As many physician mentors have cautioned me, the road to medicine and patient care is long and arduous — but from where I am right now in my career, I believe building this depth as a clinician is worth the investment.

MD and Managing Deal-flow

As an investor, more so than any other career that I’ve come to know, you have the unparalleled opportunity to build meaningful connections as a full-time job: whether it’s through meeting and supporting entrepreneurs, bringing together domain experts for due diligence, or growing portfolio companies — I know that my natural aptitude for connecting people is a foundational element of the venture capitalist position. If practicing medicine “zooms in” from the lens of product management to care for individuals at the patient-level, venture capital offers the complementary “zoomed-out” lens to care broadly for many individuals (whether entrepreneurs or the people the company serves).

Before I jump into medicine to fully invest my career clinical depth and expertise, I feel uniquely drawn to the scale at which a venture capital firm operates and the broad intuition they bring to their industries. I also believe that the opportunity to work with a technology-oriented (vs. industry-specific) firm is mutually aligned with my short-term interests in building an investor’s intuition and long-term interests in bringing insights from technology into medicine/healthcare over the course of my career as a physician.

Building Breadth and Depth

To me, the practice of medicine and an innovator’s mindset are inextricably tied — each naturally enables and informs the other. I will continue to deepen my regular touch points with medicine through the number of formative clinical volunteering experiences I will continue to have in Boston, but intend on joining an exciting venture capital firm (which I will formally announce in a separate post) that has been graciously supportive of my interests in medicine and aligns strongly with my values in community-building and investing in people.



Sherman Leung

Investing @AlleyCorp, aspiring physician-investor/innovator