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Tips for Entrepreneurs from a First Year VC



A close friend of mine likes to joke about how entrepreneurs & operators who become venture capitalists are “trading in their blue light sabers for red ones” – it’s a funny analogy…naturally, comparing investors to Sith Lords seems to fit pretty well some days.

But the benefit of switching from one side to the other is that perspective can sometimes be illuminated. After nearly 20 years of operating at places like Mozilla, Reactivity, Trilogy & Apple, I still tend to think like an entrepreneur myself, so some of the assumptions of life inside a VC are maybe a little more obvious to me than folks who have been around longer.

So here are some observations about my first year of VC life, and then some of the ways that being on the “inside” has changed the way I think that entrepreneurs should think about approaching investors – things I wish I had understood myself when I was pitching.

A Year of Observations about VC Life 

Life as a VC is a sea of meetings. Really, it is a lot of meetings. Most of them are single meetings, with no follow-ups. Most don’t result in an investment in a company at all. In 2011 I had first meetings with just over 350 companies, plus another 100 more as parts of business plan judging and demo days. Those meetings resulted in just four investments for me (Tumblr, Dropbox, Clearslide and Citrus Lane) plus a handful of seed investments.

That’s a massive “bias-to-no” for any profession – 99% or so. It’s a tough negative bias, and every investor I know is affected by it in some way. But that one percent is like a lightning strike: those meetings can form the basis for some of the most interesting and meaningful work you’ll ever do.

High fidelity communication is impossible. Because so many meetings are one-offs like I described, it’s very hard to communicate effectively. As an operator, you get good at being direct with the people you work with – or you fail.

In the context of a startup, relationships are developed over a period of months or years, so that candor can be better understood and more nuanced, resulting in communications that are efficient and effective, without hurt feelings from misunderstandings.

Venture meetings aren’t like that. They’re incredibly overloaded: you’re trying to have a really good communication about who you are, what you’ve built, and how you want to grow. And you’re trying to do it in what is very often an extremely emotionally significant context of someone putting everything at risk to change the world. All with no existing relationship context to fall back on.

As an investor, I feel that a situation like that deserves my fullest possible attention, and my best questions about and suggestions for the business. But since we’ve never interacted before, there’s the danger of seeming too harsh in cases like that – we don’t have the shared context, vocabulary and trust frameworks in place that you do in longer term relationships. I think that’s why so many investors are often vague or non-responsive in their interactions afterwards – something I’ve tried very hard to avoid, although with imperfect success so far.

Timing is everything, and everyone is multi-tasking. This applies to both the startup and the investor I’ve found – because each has their own set of work going, and any number of competing projects and priorities. The right thing coming by at the wrong time can be as challenging as an investment that just isn’t a natural fit. Life as a VC has different patterns and rhythms than life for operators – the nature of VC work is that you’ve got multiple companies and entrepreneurs you’re working with all the time, plus a constant stream of new folks to meet, and often in wildly different domains.

This means constant context switching, and there are times when excellent entrepreneurs and startups come through when it’s just hard or impossible to take focus from existing or in process investments. That creates a severe asymmetry: as an entrepreneur, you’re thinking about one thing (broadly defined as your startup), deeply,all the time, while investors that you’re talking with are trying to juggle many at once.

Venture firms and partners are idiosyncratic and highly personal. When I raised money for my own startup, I didn’t know much about how to think about approaching VCs. I knew folks at various firms, and mostly went to talk with those who I knew and then went through their process over the subsequent several weeks. I figured that VCs were all mostly similar to each other.

I’ll say candidly that in my case, I was extremely lucky when that “strategy” worked – my investors were Mitch Kapor and Peter Fenton when they were both at Accel Partners – they were incredibly great for us, and I’ve had fantastically productive relationships with both for more than a decade now. But at some level it was really just dumb luck. I could easily have found a firm and partners who wouldn’t have worked.

Every firm has different culture: some are collaborative, others more solo practices; a small few (including Greylock) consist of former or current entrepreneurs, other firms consist of people who have been investors most of their careers; some are progressive, some are conservative. And even in partnerships, everyone there is different. Different in interests, skills, capabilities, stage in life, and temperament, at the very least.

But here’s the thing: meeting with an amazing entrepreneur can change your whole year. 

That’s why you do it. To find people to change the world with. I’ve been very lucky this year to work with some incredible entrepreneurs and teams, not just limited to the companies we were able to invest in. And that’s what we’re all looking for: not just the opportunity to make great investments, but the chance to work with people who are setting out to make the world the way they want it. There’s no more optimistic and hopeful endeavor, and it’s 100% addictive.

Suggestions on Interacting with VCs

Given that context on what it’s like to be on the inside of a VC firm, here are some things I wish I had understood when I pitched myself.

  1. Be human; be yourself. Be prepared and have a pitch, but be willing to go off script. Talk about the parts of what you’re doing that are the most exciting to you! And in general, it’s probably best not to just jump into a PowerPoint deck. Take a few minutes to introduce yourself, and hear a bit from who you’re seeing. Don’t get too informal, of course – you’re still in a business context – but try to interact in as authentic a working style as you can.
  2. Seek out investors who lean forward, who engage, who ask you tough questions. Tough questions aren’t always fun, but they’re ultimately what makes your company better.
  3. You should ask questions, too, particularly to understand how the investor thinks about businesses like yours. I personally love getting questions and like a spirited debate. Helps us get to know each other.
  4. Be resilient. A “no” from a few partners or firms doesn’t mean you won’t get funded. As mentioned above, a lot of times it’s context.
  5. Be persistent. A “no” on this round doesn’t mean that an investor won’t be better, or more able to work on your company in the next round.
  6. Remember that relationships are progressions. Don’t read too much into any particular interaction. Some investors ask a bunch of questions in first meetings. Some listen more and engage more as the process goes on. Everyone is different. When in doubt about what they’re thinking, ask!
  7. Above all, don’t think of fundraising as a transaction to get finished and move onto the next thing. It is important to get the funding you need, but you’ll live with your investor for the life of your startup (and really beyond, relationship-wise). Think about it like the balancing act when you’re trying both to attract and evaluate an all-star member of your team.

Your mileage may vary, of course. But hopefully this bit of context will make the difference for you between just a pitch meeting and the start of a world-changing new relationship.

This article was written by John Lilly, a partner at Greylock Partners. Prior to Greylock, John was CEO of Mozilla, makers of Firefox. In addition to leading Greylock’s investments in Tumblr, Dropbox, Clearslide and Citrus Lane, he’s also on the boards of directors of Mozilla and Code for America. He has written articles for Pandodaily, as well as maintains his own blog.


“When Adam Draper does Crypto Standup, Singapore listens”



I live and work in Singapore and Santa Monica. Yes, I am blessed. However, my life has been by design, I think of what I want and so I make my life choices and make them happen in my life. Hence the bi-continent living and that comes with bi-continent and now global community living, being and ecosystems building. So I am now never surprised when one part of my world meets another.

I went to Wavemaker Partners venture capital event this evening, keen to meet Adam Draper, who is one of the many great presenters at Crypto Invest Summit, April 30- May 2 in Los Angeles.

Since I actively support leaders who are building scalable, sustainable businesses and movements for the betterment of many; of course I am learning about Blockchain and Cryptocurrency. I had been keen to report on the Crypto Invest Summit as I would be back in May to LA for my PhD programme. I was in communications with the organizers. However, I am being awarded an award at the Women Economic Forum in Delhi that same week and could not be physically present.

Still I wanted to report on the event, somehow.

I wanted to listen to the speakers and support some of the speakers who are already friends and experts I rely on for greater insights on cryptocurrency. I like learning and sharing with the greater audience, I have in Asia what I am learning from the US and vice versa. So I feel I had my chance tonight to do a bit of that.

I could not help but smile as Adam Draper shed light into his world of investing in more than 85 crypto related products because he was such a breath of fresh air to the last few Blockchain and Financial conferences I have been reporting on; especially here in Asia.

He just says it like it is.

He kept stopping the audience when they said Blockchain and he said, “You know you really mean cryptocurrency.”  He hit the nail on the head because I have seen so clearly how this phrase had been said in Singapore time and again – “I am not into cryptocurrency but I believe in Blockchain.”

When he said how there was an incongruity as he sat across bankers who personally invested in cryptocurrency and when faced with an inbound of requests from their clients on the same investment; are tied by regulations and are unable to respond.

Here’s some of his best lines. If you don’t laugh or “ah-ha” the way I did, you probably just had to be there. The truth is funny because it calls out for something we all see but sometimes just do not want to admit.

There is a growing understanding of the underlying thematics that the cryptocurrency world has been experiencing as the interface between centralize; de-centralize and personal autonomy becomes more and more apparent and lines get drawn.

Adam Says:

1) The newest phenomenon is that some of the ICO founders are now just so rich from their ICOs that they really don’t need to work on the project they asked for money for.

2) For the crypto-world, money doesn’t matter anymore!
They need talent

It’s so founder friendly now.

3) What Bitcoin made us ask is “What is money?”

The next question is “What is government and governance?”

He highlighted if an entrepreneur is looking for a problem to solve., then the entrepreneur is always looking for horrible industries with poor services and high costs. So yes – Governments are those horrible industries and they need to be disrupted.

4)  Any company who comes to an investor and leads with how much ICO has raised; is a red flag. Leave immediately and go read a Harry Potter book instead.
If they are leading with value and not the problem they are solving. Beware. (read more here

5) If you are going to invest in where the brains are. It’s in crypto.

6) Philosophically, Coinbase is against ethos of what Bitcoin and the cryptocurrency movement is trying to do. However to do such a move from fiat to digital currency, there would need a way to do that. So Coinbase acts like a browser does for internet. One day there will be no need to cash in or out as everyone is already there on digital. Cryptocurrency is the exchange of value. His advice and we know his bias as he is invested in  Coinhako; is to hold onto an exchange for 3-5 years since onboarding of all users to the new digital currency will take some time.

Adam met with many banks and government bodies on his trip to Singapore – I hope they got his truths.

I ended the night by thanking Adam for making me laugh. He reminded me of how much I miss LA.

Want more of this?

If you are in LA on April 30 – May 2.



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Callum Connects

Adrian Reid, Founder of Enlightened Stock Trading



Adrian Reid escaped the rat race and became a knowledgeable trader. He now shares his trading knowledge and empowers others to take control of their stocks.

What’s your story?
After working 12-16 hour days in the corporate world for many years I had a moment of realisation on the 1 hour bus ride to work. It was here at this moment in time, I realised that I felt trapped, desperate and isolated. Trapped in a job I hated, and a life I had not designed. I had long been interested in investing, but I made the decision at that point to become the best trader I could possibly be and escape the rat race.
My dream was to be free; free of the 9 to 5, the commute, the stress and the exhaustion. I threw myself into my stock trading research and study and emerged 3 months later with the trading rules that would ultimately buy me my freedom. I am now retired from the corporate world, I trade full time and share my knowledge with other aspiring traders through my online education program which puts them in control and empowers them to take control and accountability for their trading results.

What excites you most about your industry?
So many people are trapped in jobs they don’t like or are feeling immense financial pressure in their life. Trading education is typically done extremely badly today because of the conflicts of interest in the industry. Fund managers want to hold onto your money forever; brokers want you to trade more frequently; forex brokers want you to use more leverage. Why? Because that is how they make their money.
By teaching traders how to develop and test their own stock trading systems I am able to empower them to find trading rules which fit their own personality, objectives and lifestyle. This is the only way for new traders to be successful. This process transforms people’s financial future, their relationship with money and wealth and gives them hope. I love that!

What’s your connection to Asia?
I recently spent 3 years living in Singapore which I absolutely loved. This put me in a good position to observe the other Asian markets. As a stock trader I am interested in many markets and economies around the world, however the Asian markets have some of the best potential for trading profits. I have traded stocks in Hong Kong, Shanghai and Tokyo and I have developed trading systems that work in many other Asian markets as well.

Favourite city in Asia for business and why?
My favourite city is Singapore. After living in Singapore for 3 years my family fell in love with the city. Life is great in Singapore for the whole family and the pro-business and investing policies of the government make it a wonderful place to build your financial future as well.

What’s the best piece of advice you ever received?
On a personal front: Find something you love, throw all your energy and passion into it.
On the wealth front: Spend less than you earn and invest the difference. Take control of your finances and always accept 100% responsibility for your investment decisions.

Who inspires you?
My wife Stephanie inspires me. Her commitment to everything she does, her compassion, her insights into people and her ability to uplift those around her, make me want to be a better person.

What have you just learnt recently that blew you away?
No matter what we think we know, there will always be a different perspective that can change our opinion. In my own trading, I continually find that the truths I cling to are not absolute and they can be misleading if held onto dogmatically. Striking a balance between taking a stance and knowing when to change that stance based on new information is critical in all areas of life.

If you had your time again, what would you do differently?
I would have taken more action earlier on. My fear of mistakes (which still limits me on occasions, like most people) has always proven to be baseless. Playing small to avoid the embarrassment or pain of mistakes is very limiting and I would have taken more action earlier, if I had my time again.

How do you unwind?
To unwind I like to read, meditate, run and ride my mountain bike in the forest.

Favourite Asian destination for relaxation? Why?
I just love the small island resort at Batu Batu. It is beautiful, isolated, quiet and surrounded by clean water, full of sealife. After a week at the resort I felt like a different person.

Everyone in business should read this book:
The Pyramid Principle by Barbara Minto. This book teaches the art of clear and structured communication. My time working as a business strategy consultant gave me a great appreciation for the importance of communication in business. Clear and effective communication can solve a myriad of challenges in your business and professional life, and as a strong communicator your employment prospects, business relationships, team performance and family life are all dramatically improved.

Shameless plug for your business:
Enlightened Stock Trading ( is the only stock market trading education business that empowers you, as an individual trader. It shows you how to design and test your own unique stock trading system that fits YOUR Personality, Objectives and Lifestyle. We have no conflicts of interest and we are focused on teaching you how to trade stocks profitably in a way that fits your life.
After working through the Enlightened Stock Trader Certification Program you will find yourself confident and empowered with your own battle tested trading system and trading plan to guide you through the markets.

How can people connect with you?
Email me directly at [email protected] or through my Facebook Page (

Twitter handle?

This interview is part of the ‘Callum Connect’ series of more than 500 interviews

Callum Laing is an entrepreneur and investor based in Singapore. He has previously started, built and sold half a dozen businesses and is now a Partner at Unity-Group Private Equity and Co-Founder of The Marketing Group PLC. He is the author two best selling books ‘Progressive Partnerships’ and ‘Agglomerate’.

Connect with Callum here:
Download free copies of his books here:

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