In September 2018, legendary venture capitalist and Benchmark General Partner Bill Gurley returned to his alma mater in Texas to deliver a presentation on rewarding careers.

Here are Gurley's 5 key tips:

Let's look a little more closely at tips 4 and 5 with the help of Blake Robbin's excellent transcription. Some of the stand-out excerpts are:

Always share best practices and don't worry about any proprietary knowledge. It's not a zero-sum game.
The activity of sharing with mentors and peers will lead to so many positive things that will help you go up, that whatever the negative costs are — they aren't going to come anywhere close.
Send letters, send gifts, anytime you accomplish something in your career. Take the time to send messages back to the people that helped you.

Gurley wraps up tip 5 with this quote from Danny Meyer's book 'Setting The Table':

I am convinced that you get what you give, and you get more by giving more. Generosity of spirit and a gracious approach to problem solving are, with few exceptions, the most effective way to earn lasting goodwill for your business.

Evolutionary biologists contend that the concept of reciprocity is encoded in our genes. The argument goes that those who helped others were likely to receive help in return and would then be more likely to survive and pass on their genes. That's intuitive enough, but let's think about it a different way.

Newton's Third Law of Motion

Shane Parrish of Farnham Street is one of my favourite thinkers and in my view the foremost authority on mental models, a concept popularised by Charlie Munger.

Mental models are reference points of understanding. They are how we understand the world. Munger believes in collecting models across disciplines - psychology, literature, science and so on. By collecting models across disciplines, you are cultivating a toolbox of lenses through which you can analyse problems, which leads to better decision-making. The below graphic illustrates how Munger thinks about a latticework of mental models - "Exactly the same sort of pattern that graces backyards everywhere, a lattice is a series of of points that connect to and reinforce each other".

Parrish is an ardent Munger disciple and recently began publishing The Great Mental Models Project, a series of four volumes that build upon each other to provide readers with a latticework of mental models. Volume 2 distils mental models from Physics, Chemistry and Biology, providing new ways of looking at the world by applying concepts from the natural sciences.

Newton's Third Law of Motion states:

For every action, there is an equal and opposite reaction.

Put another way:

Every force involves the interaction of two objects where the force asserted by one is reciprocated with an equally powerful and directionally opposite force by the other object

This law of the physical world helps us think about reciprocity in a new light. As Parrish puts it in the book:

In the physical world, the law of reciprocity works 100% of the time.
In the biological world, reciprocity doesn't have the same record. However, it has been discovered to work much more often than not, and thus harnessing it has significant long-term benefits

There are two types of reciprocity: direct and indirect. The former is simple enough quid pro quo reciprocity - I help you, you help me. The latter can be broken down into two types: pay-it-forward ("I help you and then you help someone else") and reputation building ("I help you, building a reputation as someone who helps, so that someone else helps me in the future.")

Indirect reciprocity underpins Gurley's tips for a rewarding career. Sharing best practices with your peers without fear of ceding some sort of advantage will, in aggregate, serve you far better in the long-run than holding on dearly to an ephemeral 'edge'.

Let's consider this reciprocity from the lens of startups. Being an entrepreneur is hard enough; Elon Musk compared it to "eating glass and staring into the abyss of death". Now you have to be nice to other founders and share best practices? Surely that's too much? What about that one time you did someone a favour and then they never so much as thanked you let alone returning the favour?

Just like the time you smiled at a stranger and they didn't smile back, you're likely to vividly remember those instances where favours you did for others weren't returned. As Parrish argues, loss aversion is baked into our DNA; those who prioritised the mitigation of threats such as the negative experience of a loss (when you put yourself out there and receive nothing in return) had a higher chance of survival than those who prioritised opportunities.

That said, if you tally up the outcomes of positive reciprocal behaviour over a longer period, you'll surely find that the benefits far outweigh the negative experiences. Reflect for a moment on your own experiences. Sure, you can probably recall many instances of helping others where you didn't receive anything in return directly, but the trick is to think in the aggregate.

That's one of the reasons why communities have blossomed, where members share best practices, knowledge and experiences without a second thought. Here are just a few of the many communities in the UK whose members never fail to amaze me with their generosity towards each other:

  • Campus London- hundreds of resident founders of Google's Startup Campus in London share best practices and knowledge with each other over Slack.
  • YSYS - diverse founders share how they are navigating the entrepreneurial journey, which comes with its added challenges as a BAME founder.
  • Femstreet - global community for women in tech with hundreds of members who have helped each other through jobs, introductions and advice.
  • Bunch of founders - this is a relatively new community that is also focused on helping underrepresented founders and has already helped them find co-founders and access investors.
  • Secretive VC communities that I can't name for fear of being exiled. I kid. Zoe Peden's FutureWorldVC, Diversity VC's Future VC and many more communities exist for the purpose of helping new and aspiring investors to connect with each other and share knowledge.
  • There are so many niche communities out there - Out of Hours (for those with a side project), Zebras Unite (advocating for more inclusive VC), Indie Hackers (turning your side hustle into a business) to name just a few.

This isn't a zero-sum world. Those people helping each other without expecting anything in return - the paying-it-forward types - are not mad.

People tend to receive what they offer to the world. Thus, to change our world, we must change what we offer to others.

This quote from J.D. Salinger beautifully captures the sentiment behind mentorship:

Many, many men have been just as troubled morally and spiritually as you are right now. Happily, some of them kept records of their troubles. You'll learn from them-if you want to. Just as someday, if you have something to offer, someone will learn something from you. It's a beautiful reciprocal arrangement.

The VCs who are revered today were once the beneficiaries of unique mentorship themselves. In an essay on the qualities that make up great VCs, Steve Schlafman alludes to the unique experiences of great investors and asks us to ponder things like:

"Did Bill Gurley receive years of unique mentorship from the founding partners of Benchmark?".
"Did Michael Moritz discover the ideal founder archetype by writing about Steve Jobs and Lee Iacocca or did he learn from Don Valentine and his predecessors at Sequoia Capital?"

Good mentors are hard to find. Naturally, as a junior VC, you would hope that a partner takes you under their wing and passes down all the wisdom they have accumulated over the years. That's just not always the case. Mentors are even more important for founders; the trials and tribulations of the entrepreneurial journey are easier to confront when you have been able to learn from those who have trod the same path. Salinger's words are most apt here.

That's why Gurley's advice is so valuable. When you find a mentor, make them invested in your journey. Reciprocate their support by continuously reminding them of how they have positively affected your development. As you eventually ascend up the ladder, it's important to look back down and help those who are in the same place you were many years ago, looking upwards for help.

Thanks for reading. This post was a departure from the analyses I have done to date, but I hope you enjoyed it. I'll be writing on Mental Models in the future, so let me know your thoughts.

Deals of the week

🗳️ London-based Commonplace raises £3m from Beringea to facilitate closer collaboration between local councils and residents. The voice of residents on things like cycling paths and car-free zones is even more important in a post-COVID world, as cities attempt to transition towards more eco-friendly transport.

🏠 Selina Finance raises $53m from Global Founders Capital and Picus Capital to expand its lending operation for SMEs. Selina's USP? It allows business owners to use their homes as collateral for the loans and significantly speeds up the process compared to banks. The company is focused on 'prime' customers and has had zero defaults in its one-year existence, with plans to expand to consumer borrowing soon.

🛍️ Weezy raises a £1m pre-seed round from Heartcore Capital to expand the UK's first on-demand supermarket. Hyperlocal fulfilment centres enable deliveries in 15 minutes. It's currently serving customers in Chelsea and Fulham, with plans for up to 15 more fulfilment centres in London by the end of the year

Bramble Energy raised £5m from BGF and others to accelerate development of its hydrogen fuel cell technology. The company is a spinout from UCL and Imperial College London and claims to have developed tech capable of producing gigawatts of hydrogen fuel cells using existing global manufacturing resources.

💬 Novoic raises £2m from Anthemis, Entrepreneur First, Plug and Play Ventures and others to continue developing its speech-based AI diagnosis technology. It's currently focusing on diagnosis of early-stage Alzheimer's and Parkinson's disease and will use the investment build an exceptional AI research team focusing on deep analysis of audio-linguistic data for clinical applications.

Smart Reads

The European Union is holding firm to it's promise to save the planet, releasing the list of 64 "Green New Deal" startups that will receive funding from the European Innovation Council's €300m kitty.

Elad Gil breaks down SPACs. I know, I need to shut up about SPACs. Last time, I promise.

a16z come out with an incredible post on how embedded finance is scaling vertical SaaS, unlocking 2-5x more value - MUST READ.

Consumer social VC Turner Novak wrote a fascinating post on Pinduoduo, China's second largest ecommerce company and the world's most valuable company in the world never to have made a single quarter of operating profit. This is a treasure trove on a company that wants to be both "Costco and Disneyland".

Black men and women working on Wall Street share their experiences. This is a humbling read and highlights just how much still needs to change.

VC Finn Murphy of Frontline Ventures wrote a refreshing piece on the dark arts of fundraising and specifically how to maximise FOMO among investors. Read it if only for the laughs.

Podcasts, videos and threads

Naval Ravikant on the Tim Ferriss show (Feb 2016). Naval splits opinions, but he is definitely one of the most lucid thinkers I've ever heard. I guarantee you'll leave with at least one deep insight to mull over.


“Most geniuses - especially those who lead others - prosper not by deconstructing intricate complexities but by exploiting unrecognised simplicities.” - Andy Benoit