On creative questions and imaginative answers in a post-covid world

As anyone who has read my previous posts knows, I try to think like a scientist, analyzing data on everything from COVID-19 vs seasonal flu fatality rates to the factors predicting how early-stage venture capital will fare in a time of crisis. My background in statistics and market research coupled with 20+ years as an entrepreneur taught me to think skeptically, objectively and quantitatively, skills which have proven valuable in an environment of hyper-sensationalism and hyper-polarization.

But now we’re entering a new phase, a brave new post-covid world which I believe will be qualitatively different than the pre-covid world in many ways. Navigating this world requires a different type of thinking, closer to that of a science fiction writer than a scientist. With so much change occurring in such a short amount of time, making data-driven predictions based upon historical patterns isn’t as useful as thinking creatively about which new questions to ask and imaginatively when answering them.

In some ways, a lack of creative question-asking and imaginative question-answering is what got us into this situation in the first place. Imagine how things would have been different if political leaders were asking themselves these creative questions a few years ago:

  • How should we prepare to respond if a global pandemic hits in a few years? Do we have the ability to ramp up testing quickly? Do we have the ability to quickly survey our population to estimate infection prevalence?
  • Should we create a ‘national reserve’ of PPE for hospitals? Is there enough redundancy in our supply chain for critical goods?
  • What should be the triggers to implement mass quarantines at the state or national level? How effective will they be? What will be their health and economic consequences?

My intention isn’t to criticize politicians for not asking these questions a few years ago, because they’re only obvious in hindsight. My intention is to illustrate the importance of asking the right questions at the right time.

As a venture capital investor, it’s my job to think about how the world will look differently in the future, so that I can invest in the startups of today that stand to benefit most from the world of tomorrow.

Pre-covid this wasn’t as hard, because imagining tomorrow’s world was often just a matter of extrapolating today’s demographic trends (e.g., the aging and diversification of the American population), technological trends (e.g., mobile, AI, big data) and social trends (e.g., video sharing, online dating) into the future.

Post-covid it’s much harder, because everything changes following a Black Swan event like this. Macro trends like globalization can be quickly reversed, existing technology trends like remote work, remote education, and at-home fitness can be quickly accelerated, and new technology trends like mass infectious disease testing, optical fever detection, and mobile contact tracing can emerge.

So now I’m asking myself new questions, which can impact our fund’s investing strategy and help us frame each investing decision within the proper social, economic, political/regulatory, and health context. I’ll outline below just a few of the questions I’m now pondering.

Some of these are unique to my line of work and may reveal my own biases. My point isn’t that these are the right questions for you to ask, but rather the right types of questions to ask. A failure to ask these types of questions would leave one’s mind ill-prepared to anticipate our future post-covid reality.


  • How will 4–8 weeks of mass quarantine affect social behavior? Will people go back to bars and restaurants? If so, how long until at pre-covid levels?
  • How will travel be impacted? Will people feel safe in crowded airports? Will closing national borders make people afraid to visit other countries even post-crisis?
  • Will people still go to conferences? Will business relationships be forged as effectively behind a face mask? Without handshakes?


  • How long will it take for consumer confidence to resume? Which spend categories will cash-strapped consumers deem essential vs discretionary?
  • How will mass unemployment impact economic recovery? How will a recession impact startup valuations in 3, 6, or 12 months?
  • How will the stock market move in the coming months? How will this impact investor appetite for venture capital as an asset class?
  • What are the second and third order effects if entire economic sectors like restaurants, airlines, hotels and energy are severely handicapped?


  • How will this crisis impact the balance of power between Democrats and Republicans? Incumbents vs challengers? Trump vs Biden?
  • Will young people (who bear the brunt of lockdowns) revolt against older people (who reap the most benefit)? Will crime rates rise with mass unemployment? Will there be civil unrest?
  • Which regulatory regimes will change? Will the restrictions lifted on inter-state telemedicine stick? How long will the FDA’s Emergency Use Authorizations (EUAs) for COVID-19 diagnostics and therapeutics last?


  • Will the virus resume spreading once shelter-in-place ordinances are lifted? Will the public tolerate another round of SIP now that unemployment rates are so high?
  • Are there any promising COVID-19 therapeutics or vaccines on the horizon? How long would they take to come to market?
  • What will be the health impacts of SIP itself? Are mental health issues on the rise? What will be the consequences of delaying elective medical procedures? How long will people stay afraid of hospitals?

Reading over this list of questions you’d probably think I’m neurotic, but also think how neurotic the pandemic-related questions I listed above for politicians would have sounded a few years ago.

In the future, some of these questions will look crazy and others will look prescient. Right now it’s impossible to tell one from the other, so I just ask myself them all… and many more.

To quote Dwight D. Eisenhower:

In preparing for battle I have always found that plans are useless, but planning is indispensable.

Techie and investor. Founder at Rebel Fund and previously Pioneer Fund. Chairman of Infosurv/Intengo and CrowdMed (YC W13). Former Bain consultant. Data nerd.