Lessons Learned from being an Entrepreneur in Residence

Part of being highly successful is having the energy, drive, and basic intelligence you need to win. You also need the right experience and the right network of people to support you.  From reading this blog, you have probably gathered that I “cheat” at the first one – part of my energy, drive, and intelligence is artificially induced through biohacking techniques I’ve honed over the years.  Here’s a quick write-up of my experience as an Entrepreneur in Residence at Trinity Ventures last year for those readers who are interested in the rare Entrepreneur in Residence opportunity in Silicon Valley.

I’m writing this because GigaOm just published an article by Zack Urlocker, the CEO of MySQL, who sold his company for $1 billion in cash.  Zack’s article is about his time as an Entrepreneur in Residence at Scale Venture Partners, a major Silicon Valley VC.  He’s an entrepreneur’s entrepreneur.  I don’t know if he’s a biohacker, but a surprising number of executives are – they’re the ones who figure out what gets them up and keeps them doing.

I do know that a surprising number of entrepreneurs I meet are fellow biohackers in one way or another.  Most cut back on sleep but perform well.  Many use exercise to keep their brains sharp – but they use it like a drug.  A smaller, but still significant, percentage use breathing and meditation to keep themselves sharp, and many of them take supplements to support their mental function and health.

Zack does a good job explaining what an EIR does, but here’s my quick definition: being and Entrepreneur in Residence is a dream job.  You get access to unlimited start-ups, very senior people, VC business cards network, and your expenses covered.  Often, you even get a small paycheck.  Your job is to meet as many entrepreneurs as you can and to come up with your own idea to start or join a company.  It’s a privilege to be an EIR; a vote of confidence from a venture capital firm that they think you have what it takes.

Here’s the email I wrote as I transitioned out of the EIR program at Trinity to work for a start-up (two actually) and then a large security company.  It sums up what I learned about entrepreneurs, about VCs, and about my industry segment (cloud computing, security, and virtualization).


To: Everyone

I’ve had a great time as an Entrepreneur in Residence at Trinity over the last few months and now the EIR program is coming to its planned end date. I am fortunate to have met an amazing number of smart and motivated entrepreneurs, to have learned about some really compelling startups, and to get to experience first-hand the mysterious inner workings of the venture capital decision process.

You’re receiving this message because I recently used my Trinity Ventures email address to communicate with you, and I’d like you to be able to reach me. My personal email is xxxxxxxxx, my phone doesn’t change (xxxxxxx), and I’m always at www.linkedin.com/in/asprey.  

For the next 4-6 weeks l will do some advisory work and strategy consulting, help a few startups navigate the funding process, and focus in on my next senior role in cloud computing, virtualization, and SaaS, either in the Bay Area or Canada. My time is about half booked for the coming month and I have capacity to do a couple more projects for companies where I can have a big impact. In addition, my nonprofit is bringing in NY Times best-selling health author Gary Taubes to speak in Palo Alto May 20th. Please attend if you’d like! (ed note: See? Had to work in a biohacking angle!)

The big things I’ve observed as an EIR:

About entrepreneurs

1.       If you can’t say it in less than 15 slides, you need to do more work. (Read “Presenting to Win” as a start…)

2.       It’s better to say you don’t know than to answer some other question instead.

3.       Technology is cool but you’ll get a lot more attention if you have some idea of who will buy it.

About VCs

1.       Experienced VCs are like great poker players – some can read an entire room in 5 minutes and accurately predict the outcome of the pitch. How you tell your story can signal more than your story itself. (Read “Honest Signals” to find out why …)

2.       Counter to common beliefs, VCs do not typically have forked tongues or tails. (those are usually found on corpdev guys…)

3.       The most common objections to funding a company are, in order from most to least common (team, market, valuation, product)

About cloud computing and virtualization

1.     IaaS doesn’t compete with PaaS; IaaS will slowly BECOME PaaS via slow creeping automation of devops functions. Few IaaS apps will be recoded to run on PaaS. Instead, devops functions will dissolve into a variety of cloud services.  

2.     Virtual desktops are here to stay, but the TCO still isn’t very good. It’s getting better. The requirements for virtual desktops are substantially different from server virtualization. 

3.     Cloud services dealing with large data volumes should focus on data that’s already in the cloud when possible. If your plan makes customers suck an elephant’s worth of data through a soda straw of branch office bandwidth, change your target market.





Not Harder

Smarter Not Harder: The Biohacker’s Guide to Getting the Body and Mind You Want is about helping you to become the best version of yourself by embracing laziness while increasing your energy and optimizing your biology.

If you want to lose weight, increase your energy, or sharpen your mind, there are shelves of books offering myriad styles of advice. If you want to build up your strength and cardio fitness, there are plenty of gyms and trainers ready to offer you their guidance. What all of these resources have in common is they offer you a bad deal: a lot of effort for a little payoff. Dave Asprey has found a better way.

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